Tokić-Vujošević, Zorana

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  • Tokić-Vujošević, Zorana (18)

Author's Bibliography

Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study

Jakšić, Jovana; Milinković, Evgenija; Cvetanović, Katarina; Tokić-Vujošević, Zorana; Jovanov, Vladislav; Mitrović, Aleksandra; Maslak, Veselin

(Royal Society of Chemistry, 2024)

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Milinković, Evgenija
AU  - Cvetanović, Katarina
AU  - Tokić-Vujošević, Zorana
AU  - Jovanov, Vladislav
AU  - Mitrović, Aleksandra
AU  - Maslak, Veselin
PY  - 2024
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5389
AB  - In this study, we conducted a comprehensive investigation of newly synthesized fullerene derivatives developed for potential application in perovskite solar cells (PSCs). We explored three novel dihydrofuran-fused C60 fullerene derivatives (13, 14, and 15) that were specifically designed to enhance solubility and interaction with the substrate, fluorine-doped tin oxide (FTO). A comparative analysis was performed, with reference to the widely used phenyl-C61-butyric acid methyl ester (PCBM) and compound 12, from which 13, 14, and 15 are derived, to assess the impact of sugar units on materials properties. The synthesized compounds demonstrated significant solubility in common organic solvents, a critical factor in their potential application in wet-processed PSCs. Our investigation included electrochemical property analysis, thin film deposition, surface characterization, and electrochemical impedance spectroscopy (EIS). EIS measurements unveiled key insights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.
PB  - Royal Society of Chemistry
T2  - Physical Chemistry Chemical Physics
T1  - Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study
VL  - 26
IS  - 1
SP  - 517
EP  - 523
DO  - 10.1039/d3cp04322c
ER  - 
@article{
author = "Jakšić, Jovana and Milinković, Evgenija and Cvetanović, Katarina and Tokić-Vujošević, Zorana and Jovanov, Vladislav and Mitrović, Aleksandra and Maslak, Veselin",
year = "2024",
abstract = "In this study, we conducted a comprehensive investigation of newly synthesized fullerene derivatives developed for potential application in perovskite solar cells (PSCs). We explored three novel dihydrofuran-fused C60 fullerene derivatives (13, 14, and 15) that were specifically designed to enhance solubility and interaction with the substrate, fluorine-doped tin oxide (FTO). A comparative analysis was performed, with reference to the widely used phenyl-C61-butyric acid methyl ester (PCBM) and compound 12, from which 13, 14, and 15 are derived, to assess the impact of sugar units on materials properties. The synthesized compounds demonstrated significant solubility in common organic solvents, a critical factor in their potential application in wet-processed PSCs. Our investigation included electrochemical property analysis, thin film deposition, surface characterization, and electrochemical impedance spectroscopy (EIS). EIS measurements unveiled key insights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.",
publisher = "Royal Society of Chemistry",
journal = "Physical Chemistry Chemical Physics",
title = "Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study",
volume = "26",
number = "1",
pages = "517-523",
doi = "10.1039/d3cp04322c"
}
Jakšić, J., Milinković, E., Cvetanović, K., Tokić-Vujošević, Z., Jovanov, V., Mitrović, A.,& Maslak, V.. (2024). Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics
Royal Society of Chemistry., 26(1), 517-523.
https://doi.org/10.1039/d3cp04322c
Jakšić J, Milinković E, Cvetanović K, Tokić-Vujošević Z, Jovanov V, Mitrović A, Maslak V. Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics. 2024;26(1):517-523.
doi:10.1039/d3cp04322c .
Jakšić, Jovana, Milinković, Evgenija, Cvetanović, Katarina, Tokić-Vujošević, Zorana, Jovanov, Vladislav, Mitrović, Aleksandra, Maslak, Veselin, "Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study" in Physical Chemistry Chemical Physics, 26, no. 1 (2024):517-523,
https://doi.org/10.1039/d3cp04322c . .

Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60

Jakšić, Jovana; Mitrović, Aleksandra; Tokić-Vujošević, Zorana; Milčić, Miloš; Maslak, Veselin

(Royal Society of Chemistry, 2021)

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Mitrović, Aleksandra
AU  - Tokić-Vujošević, Zorana
AU  - Milčić, Miloš
AU  - Maslak, Veselin
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3982
AB  - In this study, b-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and p-electron delocalization between methano and furano fullerenes.
PB  - Royal Society of Chemistry
T2  - RSC Advances
T1  - Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60
VL  - 11
IS  - 47
SP  - 29426
EP  - 29432
DO  - 10.1039/d1ra03944j
ER  - 
@article{
author = "Jakšić, Jovana and Mitrović, Aleksandra and Tokić-Vujošević, Zorana and Milčić, Miloš and Maslak, Veselin",
year = "2021",
abstract = "In this study, b-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and p-electron delocalization between methano and furano fullerenes.",
publisher = "Royal Society of Chemistry",
journal = "RSC Advances",
title = "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60",
volume = "11",
number = "47",
pages = "29426-29432",
doi = "10.1039/d1ra03944j"
}
Jakšić, J., Mitrović, A., Tokić-Vujošević, Z., Milčić, M.,& Maslak, V.. (2021). Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances
Royal Society of Chemistry., 11(47), 29426-29432.
https://doi.org/10.1039/d1ra03944j
Jakšić J, Mitrović A, Tokić-Vujošević Z, Milčić M, Maslak V. Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances. 2021;11(47):29426-29432.
doi:10.1039/d1ra03944j .
Jakšić, Jovana, Mitrović, Aleksandra, Tokić-Vujošević, Zorana, Milčić, Miloš, Maslak, Veselin, "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60" in RSC Advances, 11, no. 47 (2021):29426-29432,
https://doi.org/10.1039/d1ra03944j . .
2
2

Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials

Jakšić, Jovana; Ostojić, Sanja; Micić, Darko; Tokić-Vujošević, Zorana; Milovanović, Jelena; Karkalić, Radovan; O'Connor, Kevin E.; Kenny, Shane T.; Casey, William; Nikodinović-Runić, Jasmina; Maslak, Veselin

(John Wiley & Sons, Ltd., 2020)

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Ostojić, Sanja
AU  - Micić, Darko
AU  - Tokić-Vujošević, Zorana
AU  - Milovanović, Jelena
AU  - Karkalić, Radovan
AU  - O'Connor, Kevin E.
AU  - Kenny, Shane T.
AU  - Casey, William
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3534
AB  - In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33°C to 66°C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schröder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.
PB  - John Wiley & Sons, Ltd.
T2  - International Journal of Energy Research
T1  - Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials
VL  - 44
IS  - 2
SP  - 1294
EP  - 1302
DO  - 10.1002/er.4934
ER  - 
@article{
author = "Jakšić, Jovana and Ostojić, Sanja and Micić, Darko and Tokić-Vujošević, Zorana and Milovanović, Jelena and Karkalić, Radovan and O'Connor, Kevin E. and Kenny, Shane T. and Casey, William and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2020",
abstract = "In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33°C to 66°C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schröder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.",
publisher = "John Wiley & Sons, Ltd.",
journal = "International Journal of Energy Research",
title = "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials",
volume = "44",
number = "2",
pages = "1294-1302",
doi = "10.1002/er.4934"
}
Jakšić, J., Ostojić, S., Micić, D., Tokić-Vujošević, Z., Milovanović, J., Karkalić, R., O'Connor, K. E., Kenny, S. T., Casey, W., Nikodinović-Runić, J.,& Maslak, V.. (2020). Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research
John Wiley & Sons, Ltd.., 44(2), 1294-1302.
https://doi.org/10.1002/er.4934
Jakšić J, Ostojić S, Micić D, Tokić-Vujošević Z, Milovanović J, Karkalić R, O'Connor KE, Kenny ST, Casey W, Nikodinović-Runić J, Maslak V. Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research. 2020;44(2):1294-1302.
doi:10.1002/er.4934 .
Jakšić, Jovana, Ostojić, Sanja, Micić, Darko, Tokić-Vujošević, Zorana, Milovanović, Jelena, Karkalić, Radovan, O'Connor, Kevin E., Kenny, Shane T., Casey, William, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials" in International Journal of Energy Research, 44, no. 2 (2020):1294-1302,
https://doi.org/10.1002/er.4934 . .
7
4
6

Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives

Petković, Miloš; Nasufović, Veselin; Đukanović, Dimitrije; Tokić-Vujošević, Zorana; Jadranin, Milka; Matović, Radomir; Savić, Vladimir

(Wiley-VCH Verlag GMBH, Weinheim, 2016)

TY  - JOUR
AU  - Petković, Miloš
AU  - Nasufović, Veselin
AU  - Đukanović, Dimitrije
AU  - Tokić-Vujošević, Zorana
AU  - Jadranin, Milka
AU  - Matović, Radomir
AU  - Savić, Vladimir
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2603
AB  - Allenamides derived from amino acids participate in the cascade transformations catalyzed by Pd-0 allowing consecutive formation of two five-membered rings. The developed methodology provides an access to annulated indoles which can be transformed to functionalized indoxyl derivatives, retaining a structural motif embedded in several natural products.
PB  - Wiley-VCH Verlag GMBH, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives
IS  - 7
SP  - 1279
EP  - 1282
DO  - 10.1002/ejoc.201600067
ER  - 
@article{
author = "Petković, Miloš and Nasufović, Veselin and Đukanović, Dimitrije and Tokić-Vujošević, Zorana and Jadranin, Milka and Matović, Radomir and Savić, Vladimir",
year = "2016",
abstract = "Allenamides derived from amino acids participate in the cascade transformations catalyzed by Pd-0 allowing consecutive formation of two five-membered rings. The developed methodology provides an access to annulated indoles which can be transformed to functionalized indoxyl derivatives, retaining a structural motif embedded in several natural products.",
publisher = "Wiley-VCH Verlag GMBH, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives",
number = "7",
pages = "1279-1282",
doi = "10.1002/ejoc.201600067"
}
Petković, M., Nasufović, V., Đukanović, D., Tokić-Vujošević, Z., Jadranin, M., Matović, R.,& Savić, V.. (2016). Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives. in European Journal of Organic Chemistry
Wiley-VCH Verlag GMBH, Weinheim.(7), 1279-1282.
https://doi.org/10.1002/ejoc.201600067
Petković M, Nasufović V, Đukanović D, Tokić-Vujošević Z, Jadranin M, Matović R, Savić V. Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives. in European Journal of Organic Chemistry. 2016;(7):1279-1282.
doi:10.1002/ejoc.201600067 .
Petković, Miloš, Nasufović, Veselin, Đukanović, Dimitrije, Tokić-Vujošević, Zorana, Jadranin, Milka, Matović, Radomir, Savić, Vladimir, "Cyclative Cascades of Allenamides Derived from Amino Acids: Synthesis of Annulated Indoxyl Derivatives" in European Journal of Organic Chemistry, no. 7 (2016):1279-1282,
https://doi.org/10.1002/ejoc.201600067 . .
13
7
11

Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)

Lazić, Jelena; Spasić, Jelena; Francuski, Đorđe; Tokić-Vujošević, Zorana; Nikodinović-Runić, Jasmina; Maslak, Veselin; Đokić, Lidija

(Srpsko hemijsko društvo, Beograd, 2016)

TY  - JOUR
AU  - Lazić, Jelena
AU  - Spasić, Jelena
AU  - Francuski, Đorđe
AU  - Tokić-Vujošević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
AU  - Đokić, Lidija
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2690
AB  - Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)
VL  - 81
IS  - 8
SP  - 871
EP  - 881
DO  - 10.2298/JSC160222053L
ER  - 
@article{
author = "Lazić, Jelena and Spasić, Jelena and Francuski, Đorđe and Tokić-Vujošević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin and Đokić, Lidija",
year = "2016",
abstract = "Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)",
volume = "81",
number = "8",
pages = "871-881",
doi = "10.2298/JSC160222053L"
}
Lazić, J., Spasić, J., Francuski, Đ., Tokić-Vujošević, Z., Nikodinović-Runić, J., Maslak, V.,& Đokić, L.. (2016). Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 81(8), 871-881.
https://doi.org/10.2298/JSC160222053L
Lazić J, Spasić J, Francuski Đ, Tokić-Vujošević Z, Nikodinović-Runić J, Maslak V, Đokić L. Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society. 2016;81(8):871-881.
doi:10.2298/JSC160222053L .
Lazić, Jelena, Spasić, Jelena, Francuski, Đorđe, Tokić-Vujošević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, Đokić, Lidija, "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)" in Journal of the Serbian Chemical Society, 81, no. 8 (2016):871-881,
https://doi.org/10.2298/JSC160222053L . .
1
1
1

Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst

Radivojević, Jelena; Minovska, Gordana; Senerović, Lidija; O'Connor, Kevin; Jovanović, Predrag; Savić, Vladimir; Tokić-Vujošević, Zorana; Nikodinović-Runić, Jasmina; Maslak, Veselin

(Royal Soc Chemistry, Cambridge, 2014)

TY  - JOUR
AU  - Radivojević, Jelena
AU  - Minovska, Gordana
AU  - Senerović, Lidija
AU  - O'Connor, Kevin
AU  - Jovanović, Predrag
AU  - Savić, Vladimir
AU  - Tokić-Vujošević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2107
AB  - Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.
PB  - Royal Soc Chemistry, Cambridge
T2  - Russian Journal of Genetics
T1  - Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst
VL  - 4
IS  - 105
SP  - 60502
EP  - 60510
DO  - 10.1039/c4ra05517a
ER  - 
@article{
author = "Radivojević, Jelena and Minovska, Gordana and Senerović, Lidija and O'Connor, Kevin and Jovanović, Predrag and Savić, Vladimir and Tokić-Vujošević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2014",
abstract = "Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Russian Journal of Genetics",
title = "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst",
volume = "4",
number = "105",
pages = "60502-60510",
doi = "10.1039/c4ra05517a"
}
Radivojević, J., Minovska, G., Senerović, L., O'Connor, K., Jovanović, P., Savić, V., Tokić-Vujošević, Z., Nikodinović-Runić, J.,& Maslak, V.. (2014). Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in Russian Journal of Genetics
Royal Soc Chemistry, Cambridge., 4(105), 60502-60510.
https://doi.org/10.1039/c4ra05517a
Radivojević J, Minovska G, Senerović L, O'Connor K, Jovanović P, Savić V, Tokić-Vujošević Z, Nikodinović-Runić J, Maslak V. Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in Russian Journal of Genetics. 2014;4(105):60502-60510.
doi:10.1039/c4ra05517a .
Radivojević, Jelena, Minovska, Gordana, Senerović, Lidija, O'Connor, Kevin, Jovanović, Predrag, Savić, Vladimir, Tokić-Vujošević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst" in Russian Journal of Genetics, 4, no. 105 (2014):60502-60510,
https://doi.org/10.1039/c4ra05517a . .
3
3
2

Substituted proline derivatives as organocatalysts in the Michael reaction

Jovanović, Predrag; Ranđelović, Jelena; Ivković, Branka; Suteu, Cristina; Tokić-Vujošević, Zorana; Savić, Vladimir

(Srpsko hemijsko društvo, Beograd, 2014)

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Ranđelović, Jelena
AU  - Ivković, Branka
AU  - Suteu, Cristina
AU  - Tokić-Vujošević, Zorana
AU  - Savić, Vladimir
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2098
AB  - Chiral, polysubstituted proline esters, obtained via cycloaddition reactions of azomethine ylides, were studied as organocatalysts in the Michael reaction of aldehydes/ketones and vinylsulphones. Under optimised reaction conditions employing 10 mol % of the catalyst in wet CH2Cl2, the yields of the products were generally good while the enantioselectivity varied, reaching up to 52 %.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Substituted proline derivatives as organocatalysts in the Michael reaction
VL  - 79
IS  - 7
SP  - 767
EP  - 778
DO  - 10.2298/JSC131015002J
ER  - 
@article{
author = "Jovanović, Predrag and Ranđelović, Jelena and Ivković, Branka and Suteu, Cristina and Tokić-Vujošević, Zorana and Savić, Vladimir",
year = "2014",
abstract = "Chiral, polysubstituted proline esters, obtained via cycloaddition reactions of azomethine ylides, were studied as organocatalysts in the Michael reaction of aldehydes/ketones and vinylsulphones. Under optimised reaction conditions employing 10 mol % of the catalyst in wet CH2Cl2, the yields of the products were generally good while the enantioselectivity varied, reaching up to 52 %.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Substituted proline derivatives as organocatalysts in the Michael reaction",
volume = "79",
number = "7",
pages = "767-778",
doi = "10.2298/JSC131015002J"
}
Jovanović, P., Ranđelović, J., Ivković, B., Suteu, C., Tokić-Vujošević, Z.,& Savić, V.. (2014). Substituted proline derivatives as organocatalysts in the Michael reaction. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 79(7), 767-778.
https://doi.org/10.2298/JSC131015002J
Jovanović P, Ranđelović J, Ivković B, Suteu C, Tokić-Vujošević Z, Savić V. Substituted proline derivatives as organocatalysts in the Michael reaction. in Journal of the Serbian Chemical Society. 2014;79(7):767-778.
doi:10.2298/JSC131015002J .
Jovanović, Predrag, Ranđelović, Jelena, Ivković, Branka, Suteu, Cristina, Tokić-Vujošević, Zorana, Savić, Vladimir, "Substituted proline derivatives as organocatalysts in the Michael reaction" in Journal of the Serbian Chemical Society, 79, no. 7 (2014):767-778,
https://doi.org/10.2298/JSC131015002J . .
5
5
5

A Useful Synthetic Equivalent of a Hydroxyacetone Enolate

Bigović, Miljan; Maslak, Veselin; Tokić-Vujošević, Zorana; Divjaković, Vladimir; Saičić, Radomir N.

(Amer Chemical Soc, Washington, 2011)

TY  - JOUR
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Divjaković, Vladimir
AU  - Saičić, Radomir N.
PY  - 2011
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1482
AB  - Indium promoted allyiation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords and-alpha,beta-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions Into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldois.
PB  - Amer Chemical Soc, Washington
T2  - Organic Letters
T1  - A Useful Synthetic Equivalent of a Hydroxyacetone Enolate
VL  - 13
IS  - 17
SP  - 4720
EP  - 4723
DO  - 10.1021/ol2019357
ER  - 
@article{
author = "Bigović, Miljan and Maslak, Veselin and Tokić-Vujošević, Zorana and Divjaković, Vladimir and Saičić, Radomir N.",
year = "2011",
abstract = "Indium promoted allyiation of carbonyl compounds with 4-(bromomethyl)-1,3-dioxol-2-one diastereoselectively affords and-alpha,beta-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions Into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldois.",
publisher = "Amer Chemical Soc, Washington",
journal = "Organic Letters",
title = "A Useful Synthetic Equivalent of a Hydroxyacetone Enolate",
volume = "13",
number = "17",
pages = "4720-4723",
doi = "10.1021/ol2019357"
}
Bigović, M., Maslak, V., Tokić-Vujošević, Z., Divjaković, V.,& Saičić, R. N.. (2011). A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. in Organic Letters
Amer Chemical Soc, Washington., 13(17), 4720-4723.
https://doi.org/10.1021/ol2019357
Bigović M, Maslak V, Tokić-Vujošević Z, Divjaković V, Saičić RN. A Useful Synthetic Equivalent of a Hydroxyacetone Enolate. in Organic Letters. 2011;13(17):4720-4723.
doi:10.1021/ol2019357 .
Bigović, Miljan, Maslak, Veselin, Tokić-Vujošević, Zorana, Divjaković, Vladimir, Saičić, Radomir N., "A Useful Synthetic Equivalent of a Hydroxyacetone Enolate" in Organic Letters, 13, no. 17 (2011):4720-4723,
https://doi.org/10.1021/ol2019357 . .
8
5
6

Comparison of vasorelaxant effect and tolerance profile of a novel isosorbide-5-mononitrate derivative with its stereoisomer and parent drug on rat mesenteric artery

Stepanović-Petrović, Radica; Savić, Vladimir; Tomić, Maja; Tokić-Vujošević, Zorana; Simić, Milena; Stepanović, Jelena M.; Jokanović, Milan; Micov, Ana

(ECV-Editio Cantor Verlag Medizin Naturwissenschaften, Aulendorf, 2010)

TY  - JOUR
AU  - Stepanović-Petrović, Radica
AU  - Savić, Vladimir
AU  - Tomić, Maja
AU  - Tokić-Vujošević, Zorana
AU  - Simić, Milena
AU  - Stepanović, Jelena M.
AU  - Jokanović, Milan
AU  - Micov, Ana
PY  - 2010
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1337
AB  - Background/Aims: 5-Ketoximeisosorbide-2-mononitrate (50-IS-2-MN) was synthesized and its pharmacological and toxicological characteristics were examined and compared with its parent drug, isosorbide-5-mononitrate (IS-5-MN, CAS 16051-77-7), and its diastereoisomer 2-ketoximeisosorbide-5-mononitrate. Methods: Vasorelaxation was studied on phenylephrine-precontracted rat superior mesenteric artery rings in organ bath procedure. In some rings, the endothelium was mechanically removed. In vitro tolerance was induced by treating the precontracted rings with maximal concentrations of the parent drug and the ketoximes, and after washing out, the procedure was repeated for two times. Furthermore, rats were treated with a single oral dose (1000 mg/kg) of 50-IS-2-MN and 20-IS-5-MN. Results: After a phenylephrine-induced contraction, 50-IS-2-MN (10(-8)-10(-4) mol/l) caused a concentration-dependent relaxation of the rat superior mesenteric artery that was strongly potentiated after the removal of the vascular endothelium. In preparations with or without endothelium, 50-IS-2-MN was a more potent relaxant than either the parent compound or its isomer. The mechanism of the relaxant effect of 50-IS-2-MN involves the activated soluble guanylyl cyclase-cyclic GMP pathway. Hydralazine (10(-5) mol/l), a strong antioxidant, ameliorated tolerance to IS-5-MN, but did not affect the absence of tolerance to either ketoxime. The minimum lethal dose in rat for 50-IS-2-MN and 20-IS-5-MN was greater than 1000 mg/kg. Conclusion: These results suggest that the modification of the configuration at the ester carbon of IS-5-MN contributes to more potent and tolerance-devoid activity on the rat superior mesenteric artery.
PB  - ECV-Editio Cantor Verlag Medizin Naturwissenschaften, Aulendorf
T2  - Arzneimittelforschung - Drug Research
T1  - Comparison of vasorelaxant effect and tolerance profile of a novel isosorbide-5-mononitrate derivative with its stereoisomer and parent drug on rat mesenteric artery
VL  - 60
IS  - 4
SP  - 189
EP  - 197
DO  - 10.1055/s-0031-1296272
UR  - https://hdl.handle.net/21.15107/rcub_farfar_1337
ER  - 
@article{
author = "Stepanović-Petrović, Radica and Savić, Vladimir and Tomić, Maja and Tokić-Vujošević, Zorana and Simić, Milena and Stepanović, Jelena M. and Jokanović, Milan and Micov, Ana",
year = "2010",
abstract = "Background/Aims: 5-Ketoximeisosorbide-2-mononitrate (50-IS-2-MN) was synthesized and its pharmacological and toxicological characteristics were examined and compared with its parent drug, isosorbide-5-mononitrate (IS-5-MN, CAS 16051-77-7), and its diastereoisomer 2-ketoximeisosorbide-5-mononitrate. Methods: Vasorelaxation was studied on phenylephrine-precontracted rat superior mesenteric artery rings in organ bath procedure. In some rings, the endothelium was mechanically removed. In vitro tolerance was induced by treating the precontracted rings with maximal concentrations of the parent drug and the ketoximes, and after washing out, the procedure was repeated for two times. Furthermore, rats were treated with a single oral dose (1000 mg/kg) of 50-IS-2-MN and 20-IS-5-MN. Results: After a phenylephrine-induced contraction, 50-IS-2-MN (10(-8)-10(-4) mol/l) caused a concentration-dependent relaxation of the rat superior mesenteric artery that was strongly potentiated after the removal of the vascular endothelium. In preparations with or without endothelium, 50-IS-2-MN was a more potent relaxant than either the parent compound or its isomer. The mechanism of the relaxant effect of 50-IS-2-MN involves the activated soluble guanylyl cyclase-cyclic GMP pathway. Hydralazine (10(-5) mol/l), a strong antioxidant, ameliorated tolerance to IS-5-MN, but did not affect the absence of tolerance to either ketoxime. The minimum lethal dose in rat for 50-IS-2-MN and 20-IS-5-MN was greater than 1000 mg/kg. Conclusion: These results suggest that the modification of the configuration at the ester carbon of IS-5-MN contributes to more potent and tolerance-devoid activity on the rat superior mesenteric artery.",
publisher = "ECV-Editio Cantor Verlag Medizin Naturwissenschaften, Aulendorf",
journal = "Arzneimittelforschung - Drug Research",
title = "Comparison of vasorelaxant effect and tolerance profile of a novel isosorbide-5-mononitrate derivative with its stereoisomer and parent drug on rat mesenteric artery",
volume = "60",
number = "4",
pages = "189-197",
doi = "10.1055/s-0031-1296272",
url = "https://hdl.handle.net/21.15107/rcub_farfar_1337"
}
Stepanović-Petrović, R., Savić, V., Tomić, M., Tokić-Vujošević, Z., Simić, M., Stepanović, J. M., Jokanović, M.,& Micov, A.. (2010). Comparison of vasorelaxant effect and tolerance profile of a novel isosorbide-5-mononitrate derivative with its stereoisomer and parent drug on rat mesenteric artery. in Arzneimittelforschung - Drug Research
ECV-Editio Cantor Verlag Medizin Naturwissenschaften, Aulendorf., 60(4), 189-197.
https://doi.org/10.1055/s-0031-1296272
https://hdl.handle.net/21.15107/rcub_farfar_1337
Stepanović-Petrović R, Savić V, Tomić M, Tokić-Vujošević Z, Simić M, Stepanović JM, Jokanović M, Micov A. Comparison of vasorelaxant effect and tolerance profile of a novel isosorbide-5-mononitrate derivative with its stereoisomer and parent drug on rat mesenteric artery. in Arzneimittelforschung - Drug Research. 2010;60(4):189-197.
doi:10.1055/s-0031-1296272
https://hdl.handle.net/21.15107/rcub_farfar_1337 .
Stepanović-Petrović, Radica, Savić, Vladimir, Tomić, Maja, Tokić-Vujošević, Zorana, Simić, Milena, Stepanović, Jelena M., Jokanović, Milan, Micov, Ana, "Comparison of vasorelaxant effect and tolerance profile of a novel isosorbide-5-mononitrate derivative with its stereoisomer and parent drug on rat mesenteric artery" in Arzneimittelforschung - Drug Research, 60, no. 4 (2010):189-197,
https://doi.org/10.1055/s-0031-1296272 .,
https://hdl.handle.net/21.15107/rcub_farfar_1337 .

Palladium-catalyzed cross-couplings of allylic phosphates

Maslak, Veselin; Tokić-Vujošević, Zorana; Saičić, Radomir N.

(Pergamon-Elsevier Science Ltd, Oxford, 2009)

TY  - JOUR
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Saičić, Radomir N.
PY  - 2009
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1220
AB  - A range of palladium-catalyzed cross-coupling reactions can be performed using allylic phosphates as electrophiles. Both conventional heating and microwave irradiation can be used.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Palladium-catalyzed cross-couplings of allylic phosphates
VL  - 50
IS  - 16
SP  - 1858
EP  - 1860
DO  - 10.1016/j.tetlet.2009.02.026
ER  - 
@article{
author = "Maslak, Veselin and Tokić-Vujošević, Zorana and Saičić, Radomir N.",
year = "2009",
abstract = "A range of palladium-catalyzed cross-coupling reactions can be performed using allylic phosphates as electrophiles. Both conventional heating and microwave irradiation can be used.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Palladium-catalyzed cross-couplings of allylic phosphates",
volume = "50",
number = "16",
pages = "1858-1860",
doi = "10.1016/j.tetlet.2009.02.026"
}
Maslak, V., Tokić-Vujošević, Z.,& Saičić, R. N.. (2009). Palladium-catalyzed cross-couplings of allylic phosphates. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 50(16), 1858-1860.
https://doi.org/10.1016/j.tetlet.2009.02.026
Maslak V, Tokić-Vujošević Z, Saičić RN. Palladium-catalyzed cross-couplings of allylic phosphates. in Tetrahedron-Asymmetry. 2009;50(16):1858-1860.
doi:10.1016/j.tetlet.2009.02.026 .
Maslak, Veselin, Tokić-Vujošević, Zorana, Saičić, Radomir N., "Palladium-catalyzed cross-couplings of allylic phosphates" in Tetrahedron-Asymmetry, 50, no. 16 (2009):1858-1860,
https://doi.org/10.1016/j.tetlet.2009.02.026 . .
22
25
26

A useful synthetic equivalent of an acetone enolate

Maslak, Veselin; Tokić-Vujošević, Zorana; Ferjancić, Zorana; Saičić, Radomir N.

(Pergamon-Elsevier Science Ltd, Oxford, 2009)

TY  - JOUR
AU  - Maslak, Veselin
AU  - Tokić-Vujošević, Zorana
AU  - Ferjancić, Zorana
AU  - Saičić, Radomir N.
PY  - 2009
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1204
AB  - 2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed with zinc, aldol products were isolated in protected form as the corresponding MOM-enol ethers.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - A useful synthetic equivalent of an acetone enolate
VL  - 50
IS  - 48
SP  - 6709
EP  - 6711
DO  - 10.1016/j.tetlet.2009.09.113
ER  - 
@article{
author = "Maslak, Veselin and Tokić-Vujošević, Zorana and Ferjancić, Zorana and Saičić, Radomir N.",
year = "2009",
abstract = "2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed with zinc, aldol products were isolated in protected form as the corresponding MOM-enol ethers.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "A useful synthetic equivalent of an acetone enolate",
volume = "50",
number = "48",
pages = "6709-6711",
doi = "10.1016/j.tetlet.2009.09.113"
}
Maslak, V., Tokić-Vujošević, Z., Ferjancić, Z.,& Saičić, R. N.. (2009). A useful synthetic equivalent of an acetone enolate. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 50(48), 6709-6711.
https://doi.org/10.1016/j.tetlet.2009.09.113
Maslak V, Tokić-Vujošević Z, Ferjancić Z, Saičić RN. A useful synthetic equivalent of an acetone enolate. in Tetrahedron-Asymmetry. 2009;50(48):6709-6711.
doi:10.1016/j.tetlet.2009.09.113 .
Maslak, Veselin, Tokić-Vujošević, Zorana, Ferjancić, Zorana, Saičić, Radomir N., "A useful synthetic equivalent of an acetone enolate" in Tetrahedron-Asymmetry, 50, no. 48 (2009):6709-6711,
https://doi.org/10.1016/j.tetlet.2009.09.113 . .
9
5
9

Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C

Matović, Radomir; Ivković, Aleksandar; Manojlović, Marija; Tokić-Vujošević, Zorana; Saičić, Radomir N.

(Amer Chemical Soc, Washington, 2006)

TY  - JOUR
AU  - Matović, Radomir
AU  - Ivković, Aleksandar
AU  - Manojlović, Marija
AU  - Tokić-Vujošević, Zorana
AU  - Saičić, Radomir N.
PY  - 2006
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/685
AB  - The combination of ring closing metathesis and beta-fragmentation offers an efficient entry into (Z)-configured medium ring cycloalkenes. The fragmentation step can be effected under anionic or radical conditions. The versatility of this method is demonstrated by the total synthesis of (+/-)-periplanone C - a macrocyclic pheromone of Periplaneta americana.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Organic Chemistry
T1  - Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C
VL  - 71
IS  - 25
SP  - 9411
EP  - 9419
DO  - 10.1021/jo061790j
ER  - 
@article{
author = "Matović, Radomir and Ivković, Aleksandar and Manojlović, Marija and Tokić-Vujošević, Zorana and Saičić, Radomir N.",
year = "2006",
abstract = "The combination of ring closing metathesis and beta-fragmentation offers an efficient entry into (Z)-configured medium ring cycloalkenes. The fragmentation step can be effected under anionic or radical conditions. The versatility of this method is demonstrated by the total synthesis of (+/-)-periplanone C - a macrocyclic pheromone of Periplaneta americana.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Organic Chemistry",
title = "Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C",
volume = "71",
number = "25",
pages = "9411-9419",
doi = "10.1021/jo061790j"
}
Matović, R., Ivković, A., Manojlović, M., Tokić-Vujošević, Z.,& Saičić, R. N.. (2006). Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C. in Journal of Organic Chemistry
Amer Chemical Soc, Washington., 71(25), 9411-9419.
https://doi.org/10.1021/jo061790j
Matović R, Ivković A, Manojlović M, Tokić-Vujošević Z, Saičić RN. Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C. in Journal of Organic Chemistry. 2006;71(25):9411-9419.
doi:10.1021/jo061790j .
Matović, Radomir, Ivković, Aleksandar, Manojlović, Marija, Tokić-Vujošević, Zorana, Saičić, Radomir N., "Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (+/-)-periplanone C" in Journal of Organic Chemistry, 71, no. 25 (2006):9411-9419,
https://doi.org/10.1021/jo061790j . .
28
14
21

Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach

Tokić-Vujošević, Zorana; Petrović, G; Rakić, B; Matović, Radomir; Saičić, Radomir N.

(Taylor & Francis Inc, Philadelphia, 2005)

TY  - JOUR
AU  - Tokić-Vujošević, Zorana
AU  - Petrović, G
AU  - Rakić, B
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2005
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/638
AB  - Immunomodulator (-)-cytoxazone and its epimer (+)-epi-cytoxazone were synthesized starting from (D)-(-)-4-hydroxyphenylglycine. Homologation of the amino acid was achieved via the corresponding aldehyde, by a cyanohydrin reaction. The racemization of highly sensible amido aldehyde was efficiently suppressed when the oxidation of the parent aminoalcohol was performed by a modified Dess-Martin procedure.
PB  - Taylor & Francis Inc, Philadelphia
T2  - Tenside Surfactants Detergents
T1  - Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach
VL  - 35
IS  - 3
SP  - 435
EP  - 447
DO  - 10.1081/SCC-200048953
ER  - 
@article{
author = "Tokić-Vujošević, Zorana and Petrović, G and Rakić, B and Matović, Radomir and Saičić, Radomir N.",
year = "2005",
abstract = "Immunomodulator (-)-cytoxazone and its epimer (+)-epi-cytoxazone were synthesized starting from (D)-(-)-4-hydroxyphenylglycine. Homologation of the amino acid was achieved via the corresponding aldehyde, by a cyanohydrin reaction. The racemization of highly sensible amido aldehyde was efficiently suppressed when the oxidation of the parent aminoalcohol was performed by a modified Dess-Martin procedure.",
publisher = "Taylor & Francis Inc, Philadelphia",
journal = "Tenside Surfactants Detergents",
title = "Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach",
volume = "35",
number = "3",
pages = "435-447",
doi = "10.1081/SCC-200048953"
}
Tokić-Vujošević, Z., Petrović, G., Rakić, B., Matović, R.,& Saičić, R. N.. (2005). Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach. in Tenside Surfactants Detergents
Taylor & Francis Inc, Philadelphia., 35(3), 435-447.
https://doi.org/10.1081/SCC-200048953
Tokić-Vujošević Z, Petrović G, Rakić B, Matović R, Saičić RN. Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach. in Tenside Surfactants Detergents. 2005;35(3):435-447.
doi:10.1081/SCC-200048953 .
Tokić-Vujošević, Zorana, Petrović, G, Rakić, B, Matović, Radomir, Saičić, Radomir N., "Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach" in Tenside Surfactants Detergents, 35, no. 3 (2005):435-447,
https://doi.org/10.1081/SCC-200048953 . .
13
10
13

Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug

Stepanović-Petrović, Radica; Tokić-Vujošević, Zorana; Milovanović, S; Ceković, Z; Tomić, Maja

(Georg Thieme Verlag Kg, Stuttgart, 2004)

TY  - JOUR
AU  - Stepanović-Petrović, Radica
AU  - Tokić-Vujošević, Zorana
AU  - Milovanović, S
AU  - Ceković, Z
AU  - Tomić, Maja
PY  - 2004
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/476
AB  - The transformation of isosorbide-5-mononitrate (CAS 16051-77-7, IS-5-MN) to the corresponding keto derivative and its ketoxime (oxime-nitrate derivative of isosorbide) is described. The effects of IS-5-MN and the new oxime-nitrate (ON) on the endothelial and smooth muscle cells of isolated rings of the rat superior mesenteric artery were examined. After contraction induced by phenylephrine, IS-5-MN (10(-8)-10(-4) mol/1) caused a concentration-dependent relaxation. Removal of the vascular endothelium strongly potentiated this effect. On the other hand, the new ON (10(-8)-10(-4) mol/1) was a more potent relaxant than the parent drug, but its effect was not dependent on the vascular endothelium. The inhibitory effect of the artery without endothelium to the new ON was more pronounced than that to IS-5-MN. The mechanism of the relaxant effect of the new compound consisted in the liberation of nitric-oxide (NO) which activated guanylate cyclase (GC), upon which accumulation of cyclic guanosine monophosphate (cGMP) occurred, which was the second messenger leading to relaxation. Tolerance to the frequent applications of the new compound was not observed, moreover a slight increase of the effect was detected in comparison with IS-5-MN for which tolerance was observed to a great extent. Clinically, the new ON could be favorable in all types of angina in comparison with the classical IS-5-MN.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Arzneimittelforschung - Drug Research
T1  - Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug
VL  - 54
IS  - 4
SP  - 195
EP  - 202
DO  - 10.1055/s-0031-1296959
UR  - https://hdl.handle.net/21.15107/rcub_farfar_476
ER  - 
@article{
author = "Stepanović-Petrović, Radica and Tokić-Vujošević, Zorana and Milovanović, S and Ceković, Z and Tomić, Maja",
year = "2004",
abstract = "The transformation of isosorbide-5-mononitrate (CAS 16051-77-7, IS-5-MN) to the corresponding keto derivative and its ketoxime (oxime-nitrate derivative of isosorbide) is described. The effects of IS-5-MN and the new oxime-nitrate (ON) on the endothelial and smooth muscle cells of isolated rings of the rat superior mesenteric artery were examined. After contraction induced by phenylephrine, IS-5-MN (10(-8)-10(-4) mol/1) caused a concentration-dependent relaxation. Removal of the vascular endothelium strongly potentiated this effect. On the other hand, the new ON (10(-8)-10(-4) mol/1) was a more potent relaxant than the parent drug, but its effect was not dependent on the vascular endothelium. The inhibitory effect of the artery without endothelium to the new ON was more pronounced than that to IS-5-MN. The mechanism of the relaxant effect of the new compound consisted in the liberation of nitric-oxide (NO) which activated guanylate cyclase (GC), upon which accumulation of cyclic guanosine monophosphate (cGMP) occurred, which was the second messenger leading to relaxation. Tolerance to the frequent applications of the new compound was not observed, moreover a slight increase of the effect was detected in comparison with IS-5-MN for which tolerance was observed to a great extent. Clinically, the new ON could be favorable in all types of angina in comparison with the classical IS-5-MN.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Arzneimittelforschung - Drug Research",
title = "Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug",
volume = "54",
number = "4",
pages = "195-202",
doi = "10.1055/s-0031-1296959",
url = "https://hdl.handle.net/21.15107/rcub_farfar_476"
}
Stepanović-Petrović, R., Tokić-Vujošević, Z., Milovanović, S., Ceković, Z.,& Tomić, M.. (2004). Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug. in Arzneimittelforschung - Drug Research
Georg Thieme Verlag Kg, Stuttgart., 54(4), 195-202.
https://doi.org/10.1055/s-0031-1296959
https://hdl.handle.net/21.15107/rcub_farfar_476
Stepanović-Petrović R, Tokić-Vujošević Z, Milovanović S, Ceković Z, Tomić M. Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug. in Arzneimittelforschung - Drug Research. 2004;54(4):195-202.
doi:10.1055/s-0031-1296959
https://hdl.handle.net/21.15107/rcub_farfar_476 .
Stepanović-Petrović, Radica, Tokić-Vujošević, Zorana, Milovanović, S, Ceković, Z, Tomić, Maja, "Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug" in Arzneimittelforschung - Drug Research, 54, no. 4 (2004):195-202,
https://doi.org/10.1055/s-0031-1296959 .,
https://hdl.handle.net/21.15107/rcub_farfar_476 .
1
1
2

The vasoactive effect of new oxime-nitrate derived from isosorbide-5-mononitrate

Stepanović-Petrović, Radica; Tokić-Vujošević, Zorana; Milovanović, Slobodan R.; Tomić, Maja

(Savez farmaceutskih udruženja Srbije, Beograd, 2002)

TY  - CONF
AU  - Stepanović-Petrović, Radica
AU  - Tokić-Vujošević, Zorana
AU  - Milovanović, Slobodan R.
AU  - Tomić, Maja
PY  - 2002
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/407
PB  - Savez farmaceutskih udruženja Srbije, Beograd
C3  - Arhiv za farmaciju
T1  - The vasoactive effect of new oxime-nitrate derived from isosorbide-5-mononitrate
T1  - Vazoaktivna svojstva novog oksim-nitrata dobijenog iz izosorbid-5-mononitrata
VL  - 52
IS  - 4
SP  - 628
EP  - 629
UR  - https://hdl.handle.net/21.15107/rcub_farfar_407
ER  - 
@conference{
author = "Stepanović-Petrović, Radica and Tokić-Vujošević, Zorana and Milovanović, Slobodan R. and Tomić, Maja",
year = "2002",
publisher = "Savez farmaceutskih udruženja Srbije, Beograd",
journal = "Arhiv za farmaciju",
title = "The vasoactive effect of new oxime-nitrate derived from isosorbide-5-mononitrate, Vazoaktivna svojstva novog oksim-nitrata dobijenog iz izosorbid-5-mononitrata",
volume = "52",
number = "4",
pages = "628-629",
url = "https://hdl.handle.net/21.15107/rcub_farfar_407"
}
Stepanović-Petrović, R., Tokić-Vujošević, Z., Milovanović, S. R.,& Tomić, M.. (2002). The vasoactive effect of new oxime-nitrate derived from isosorbide-5-mononitrate. in Arhiv za farmaciju
Savez farmaceutskih udruženja Srbije, Beograd., 52(4), 628-629.
https://hdl.handle.net/21.15107/rcub_farfar_407
Stepanović-Petrović R, Tokić-Vujošević Z, Milovanović SR, Tomić M. The vasoactive effect of new oxime-nitrate derived from isosorbide-5-mononitrate. in Arhiv za farmaciju. 2002;52(4):628-629.
https://hdl.handle.net/21.15107/rcub_farfar_407 .
Stepanović-Petrović, Radica, Tokić-Vujošević, Zorana, Milovanović, Slobodan R., Tomić, Maja, "The vasoactive effect of new oxime-nitrate derived from isosorbide-5-mononitrate" in Arhiv za farmaciju, 52, no. 4 (2002):628-629,
https://hdl.handle.net/21.15107/rcub_farfar_407 .

Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery

Petrović, RMS; Tokić-Vujošević, Zorana; Milovanov, S; Ceković, Z; Bokonjić, Dubravko; Dobrić, Silva

(Govi-Verlag Gmbh, Eschborn, 2002)

TY  - JOUR
AU  - Petrović, RMS
AU  - Tokić-Vujošević, Zorana
AU  - Milovanov, S
AU  - Ceković, Z
AU  - Bokonjić, Dubravko
AU  - Dobrić, Silva
PY  - 2002
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/322
PB  - Govi-Verlag Gmbh, Eschborn
T2  - Pharmazie
T1  - Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery
VL  - 57
IS  - 7
SP  - 507
EP  - 508
UR  - https://hdl.handle.net/21.15107/rcub_farfar_322
ER  - 
@article{
author = "Petrović, RMS and Tokić-Vujošević, Zorana and Milovanov, S and Ceković, Z and Bokonjić, Dubravko and Dobrić, Silva",
year = "2002",
publisher = "Govi-Verlag Gmbh, Eschborn",
journal = "Pharmazie",
title = "Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery",
volume = "57",
number = "7",
pages = "507-508",
url = "https://hdl.handle.net/21.15107/rcub_farfar_322"
}
Petrović, R., Tokić-Vujošević, Z., Milovanov, S., Ceković, Z., Bokonjić, D.,& Dobrić, S.. (2002). Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery. in Pharmazie
Govi-Verlag Gmbh, Eschborn., 57(7), 507-508.
https://hdl.handle.net/21.15107/rcub_farfar_322
Petrović R, Tokić-Vujošević Z, Milovanov S, Ceković Z, Bokonjić D, Dobrić S. Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery. in Pharmazie. 2002;57(7):507-508.
https://hdl.handle.net/21.15107/rcub_farfar_322 .
Petrović, RMS, Tokić-Vujošević, Zorana, Milovanov, S, Ceković, Z, Bokonjić, Dubravko, Dobrić, Silva, "Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery" in Pharmazie, 57, no. 7 (2002):507-508,
https://hdl.handle.net/21.15107/rcub_farfar_322 .
1
3

Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives

Tokić-Vujošević, Zorana; Ceković, Z

(Georg Thieme Verlag, 2001)

TY  - JOUR
AU  - Tokić-Vujošević, Zorana
AU  - Ceković, Z
PY  - 2001
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/303
AB  - The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.
PB  - Georg Thieme Verlag
T2  - Synthesis
T1  - Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives
IS  - 13
SP  - 2028
EP  - 2034
DO  - 10.1055/s-2001-17705
ER  - 
@article{
author = "Tokić-Vujošević, Zorana and Ceković, Z",
year = "2001",
abstract = "The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.",
publisher = "Georg Thieme Verlag",
journal = "Synthesis",
title = "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives",
number = "13",
pages = "2028-2034",
doi = "10.1055/s-2001-17705"
}
Tokić-Vujošević, Z.,& Ceković, Z.. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives. in Synthesis
Georg Thieme Verlag.(13), 2028-2034.
https://doi.org/10.1055/s-2001-17705
Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives. in Synthesis. 2001;(13):2028-2034.
doi:10.1055/s-2001-17705 .
Tokić-Vujošević, Zorana, Ceković, Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives" in Synthesis, no. 13 (2001):2028-2034,
https://doi.org/10.1055/s-2001-17705 . .
3
7
8

Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates

Tokić-Vujošević, Zorana; Ceković, Z

(Freund Publishing House Ltd, London, 2001)

TY  - JOUR
AU  - Tokić-Vujošević, Zorana
AU  - Ceković, Z
PY  - 2001
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/289
AB  - A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.
PB  - Freund Publishing House Ltd, London
T2  - Heterocyclic Communications
T1  - Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates
VL  - 7
IS  - 1
SP  - 43
EP  - 48
UR  - https://hdl.handle.net/21.15107/rcub_farfar_289
ER  - 
@article{
author = "Tokić-Vujošević, Zorana and Ceković, Z",
year = "2001",
abstract = "A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.",
publisher = "Freund Publishing House Ltd, London",
journal = "Heterocyclic Communications",
title = "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates",
volume = "7",
number = "1",
pages = "43-48",
url = "https://hdl.handle.net/21.15107/rcub_farfar_289"
}
Tokić-Vujošević, Z.,& Ceković, Z.. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. in Heterocyclic Communications
Freund Publishing House Ltd, London., 7(1), 43-48.
https://hdl.handle.net/21.15107/rcub_farfar_289
Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. in Heterocyclic Communications. 2001;7(1):43-48.
https://hdl.handle.net/21.15107/rcub_farfar_289 .
Tokić-Vujošević, Zorana, Ceković, Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates" in Heterocyclic Communications, 7, no. 1 (2001):43-48,
https://hdl.handle.net/21.15107/rcub_farfar_289 .
3
4