TY  - JOUR
AU  - Marjanović, Budimir
AU  - Juranić, Ivan O.
AU  - Ćirić-Marjanović, Gordana
AU  - Mojović, M
AU  - Pasti, Igor
AU  - Janošević, Aleksandra
AU  - Trchova, Miroslava
AU  - Holler, P
AU  - Horský, J
PY  - 2012
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1806
AB  - Novel electroactive paramagnetic ethacridine oligomers were synthesized by the oxidation of ethacridine lactate with ammonium peroxydisulfate in acidic aqueous solution. The oxidative coupling of ethacridine was proved by gel permeation chromatography and MALDI-TOF mass spectrometry demonstrating the presence of oligomeric chains. Theoretical study of the mechanism of oxidation of ethacridine has been based on the semi-empirical quantum chemical computations of heat of formation and ionization energy of ethacridine, protonated ethacridine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. It was revealed that the prevalent ethacridine dimers are N(C6)C5 coupled. The influence of oxidant to monomer mole ratio on the molecular structure and the morphology of ethacridine oligomers has been studied by elemental analysis, FTIR, Raman, EPR and UV-Visible spectroscopies, MALDI-TOF mass spectrometry and scanning electron microscopy. Besides unoxidized monomeric units as prevalent, oligoethacridines contain the iminoquinonoid and newly formed fused phenazine units. The electroactivity of ethacridine oligomers was investigated by cyclic voltammetry.
T2  - Reactive and Functional Polymers
T1  - Chemical oxidative polymerization of ethacridine
VL  - 72
IS  - 1
SP  - 25
EP  - 35
DO  - 10.1016/j.reactfunctpolym.2011.10.002
ER  - 

@article{
author = "Marjanović, Budimir and Juranić, Ivan O. and Ćirić-Marjanović, Gordana and Mojović, M and Pasti, Igor and Janošević, Aleksandra and Trchova, Miroslava and Holler, P and Horský, J",
year = "2012",
abstract = "Novel electroactive paramagnetic ethacridine oligomers were synthesized by the oxidation of ethacridine lactate with ammonium peroxydisulfate in acidic aqueous solution. The oxidative coupling of ethacridine was proved by gel permeation chromatography and MALDI-TOF mass spectrometry demonstrating the presence of oligomeric chains. Theoretical study of the mechanism of oxidation of ethacridine has been based on the semi-empirical quantum chemical computations of heat of formation and ionization energy of ethacridine, protonated ethacridine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. It was revealed that the prevalent ethacridine dimers are N(C6)C5 coupled. The influence of oxidant to monomer mole ratio on the molecular structure and the morphology of ethacridine oligomers has been studied by elemental analysis, FTIR, Raman, EPR and UV-Visible spectroscopies, MALDI-TOF mass spectrometry and scanning electron microscopy. Besides unoxidized monomeric units as prevalent, oligoethacridines contain the iminoquinonoid and newly formed fused phenazine units. The electroactivity of ethacridine oligomers was investigated by cyclic voltammetry.",
journal = "Reactive and Functional Polymers",
title = "Chemical oxidative polymerization of ethacridine",
volume = "72",
number = "1",
pages = "25-35",
doi = "10.1016/j.reactfunctpolym.2011.10.002"
}

Marjanović, B., Juranić, I. O., Ćirić-Marjanović, G., Mojović, M., Pasti, I., Janošević, A., Trchova, M., Holler, P.,& Horský, J.. (2012). Chemical oxidative polymerization of ethacridine. in Reactive and Functional Polymers, 72(1), 25-35.
https://doi.org/10.1016/j.reactfunctpolym.2011.10.002

Marjanović B, Juranić IO, Ćirić-Marjanović G, Mojović M, Pasti I, Janošević A, Trchova M, Holler P, Horský J. Chemical oxidative polymerization of ethacridine. in Reactive and Functional Polymers. 2012;72(1):25-35.
doi:10.1016/j.reactfunctpolym.2011.10.002 .

Marjanović, Budimir, Juranić, Ivan O., Ćirić-Marjanović, Gordana, Mojović, M, Pasti, Igor, Janošević, Aleksandra, Trchova, Miroslava, Holler, P, Horský, J, "Chemical oxidative polymerization of ethacridine" in Reactive and Functional Polymers, 72, no. 1 (2012):25-35,
https://doi.org/10.1016/j.reactfunctpolym.2011.10.002 . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Milenković, Marina
AU  - Dilber, Sanda
AU  - Vitnik, Željko J.
AU  - Juranić, Ivan O.
PY  - 2012
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1832
AB  - A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst.
AB  - U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids
T1  - Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina
VL  - 77
IS  - 6
SP  - 741
EP  - 750
DO  - 10.2298/JSC111104016V
ER  - 

@article{
author = "Vitnik, Vesna and Milenković, Marina and Dilber, Sanda and Vitnik, Željko J. and Juranić, Ivan O.",
year = "2012",
abstract = "A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst., U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids, Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina",
volume = "77",
number = "6",
pages = "741-750",
doi = "10.2298/JSC111104016V"
}

Vitnik, V., Milenković, M., Dilber, S., Vitnik, Ž. J.,& Juranić, I. O.. (2012). Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 77(6), 741-750.
https://doi.org/10.2298/JSC111104016V

Vitnik V, Milenković M, Dilber S, Vitnik ŽJ, Juranić IO. Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society. 2012;77(6):741-750.
doi:10.2298/JSC111104016V .

Vitnik, Vesna, Milenković, Marina, Dilber, Sanda, Vitnik, Željko J., Juranić, Ivan O., "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids" in Journal of the Serbian Chemical Society, 77, no. 6 (2012):741-750,
https://doi.org/10.2298/JSC111104016V . .

TY  - JOUR
AU  - Savić, Jelena
AU  - Dilber, Sanda
AU  - Marković, Bojan
AU  - Milenković, Marina
AU  - Vladimirov, Sote
AU  - Juranić, Ivan O.
PY  - 2011
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1483
AB  - Six beta-hydroxy-beta-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus expected. The aim of this work was to determine anti-inflammatory activity, examine gastric tolerability, and to carry out molecular docking experiments to identify potential COX-2 inhibitors among the beta-hydroxy-beta-aryl propanoic acids, and to elucidate the effect a-methyl substitution on the anti-inflammatory activity. Anti-inflammatory activity and gastric tolerability were determined on rats using carragenan induced paw oedema method, and docking studies were carried out using Autodock v4.0.1. The range of ED(50) values is between 127 mu mol/kg and 15 mu mol/kg, while the result for ibuprofen is 51.7 mu mol/kg. Only slight hyperaemia or few petechiae were spotted on rat's stomach. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration, and that 2-methyl-3-hydroxy-3,3-diphenylpropanoic acid has greatest activity, surpassing that of ibuprofen, a standard NSAID. Another compound, 3-hydroxy-3,3-diphenylpropanoic acid, shows activity matching that of ibuprofen, and is non-chiral and is proven to be non-toxic. The most of investigated compounds have interactions with P3 anchor site like COX-2 selective inhibitors. No tested substances or ibuprofen produced any significant gastric lesions.
PB  - MDPI, Basel
T2  - Molecules
T1  - Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids
VL  - 16
IS  - 8
SP  - 6645
EP  - 6655
DO  - 10.3390/molecules16086645
ER  - 

@article{
author = "Savić, Jelena and Dilber, Sanda and Marković, Bojan and Milenković, Marina and Vladimirov, Sote and Juranić, Ivan O.",
year = "2011",
abstract = "Six beta-hydroxy-beta-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus expected. The aim of this work was to determine anti-inflammatory activity, examine gastric tolerability, and to carry out molecular docking experiments to identify potential COX-2 inhibitors among the beta-hydroxy-beta-aryl propanoic acids, and to elucidate the effect a-methyl substitution on the anti-inflammatory activity. Anti-inflammatory activity and gastric tolerability were determined on rats using carragenan induced paw oedema method, and docking studies were carried out using Autodock v4.0.1. The range of ED(50) values is between 127 mu mol/kg and 15 mu mol/kg, while the result for ibuprofen is 51.7 mu mol/kg. Only slight hyperaemia or few petechiae were spotted on rat's stomach. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration, and that 2-methyl-3-hydroxy-3,3-diphenylpropanoic acid has greatest activity, surpassing that of ibuprofen, a standard NSAID. Another compound, 3-hydroxy-3,3-diphenylpropanoic acid, shows activity matching that of ibuprofen, and is non-chiral and is proven to be non-toxic. The most of investigated compounds have interactions with P3 anchor site like COX-2 selective inhibitors. No tested substances or ibuprofen produced any significant gastric lesions.",
publisher = "MDPI, Basel",
journal = "Molecules",
title = "Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids",
volume = "16",
number = "8",
pages = "6645-6655",
doi = "10.3390/molecules16086645"
}

Savić, J., Dilber, S., Marković, B., Milenković, M., Vladimirov, S.,& Juranić, I. O.. (2011). Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids. in Molecules
MDPI, Basel., 16(8), 6645-6655.
https://doi.org/10.3390/molecules16086645

Savić J, Dilber S, Marković B, Milenković M, Vladimirov S, Juranić IO. Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids. in Molecules. 2011;16(8):6645-6655.
doi:10.3390/molecules16086645 .

Savić, Jelena, Dilber, Sanda, Marković, Bojan, Milenković, Marina, Vladimirov, Sote, Juranić, Ivan O., "Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids" in Molecules, 16, no. 8 (2011):6645-6655,
https://doi.org/10.3390/molecules16086645 . .

TY  - JOUR
AU  - Drakulić, Branko
AU  - Juranić, Ivan O.
AU  - Erić, Slavica
AU  - Zloh, Mire
PY  - 2008
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1029
AB  - The use of chemical penetration enhancers (CPE) is growing due to their ability to improve drug delivery through the skin. A possible mechanism of penetration enhancement could involve the complex formation between drug and components in the pharmaceutical formulation, thus altering the physicochemical properties of the active substance. Here, modelling studies indicate that hydrocarbon and oxygen-containing terpenes (penetration enhancers) could form complexes with drugs. Satisfactory correlations have been obtained between the predicted molecular properties of enhancers and their enhancement effects. Crown Copyright
PB  - Elsevier Science BV, Amsterdam
T2  - International Journal of Pharmaceutics
T1  - Role of complexes formation between drugs and penetration enhancers in transdermal delivery
VL  - 363
IS  - 1-2
SP  - 40
EP  - 49
DO  - 10.1016/j.ijpharm.2008.06.032
ER  - 

@article{
author = "Drakulić, Branko and Juranić, Ivan O. and Erić, Slavica and Zloh, Mire",
year = "2008",
abstract = "The use of chemical penetration enhancers (CPE) is growing due to their ability to improve drug delivery through the skin. A possible mechanism of penetration enhancement could involve the complex formation between drug and components in the pharmaceutical formulation, thus altering the physicochemical properties of the active substance. Here, modelling studies indicate that hydrocarbon and oxygen-containing terpenes (penetration enhancers) could form complexes with drugs. Satisfactory correlations have been obtained between the predicted molecular properties of enhancers and their enhancement effects. Crown Copyright",
publisher = "Elsevier Science BV, Amsterdam",
journal = "International Journal of Pharmaceutics",
title = "Role of complexes formation between drugs and penetration enhancers in transdermal delivery",
volume = "363",
number = "1-2",
pages = "40-49",
doi = "10.1016/j.ijpharm.2008.06.032"
}

Drakulić, B., Juranić, I. O., Erić, S.,& Zloh, M.. (2008). Role of complexes formation between drugs and penetration enhancers in transdermal delivery. in International Journal of Pharmaceutics
Elsevier Science BV, Amsterdam., 363(1-2), 40-49.
https://doi.org/10.1016/j.ijpharm.2008.06.032

Drakulić B, Juranić IO, Erić S, Zloh M. Role of complexes formation between drugs and penetration enhancers in transdermal delivery. in International Journal of Pharmaceutics. 2008;363(1-2):40-49.
doi:10.1016/j.ijpharm.2008.06.032 .

Drakulić, Branko, Juranić, Ivan O., Erić, Slavica, Zloh, Mire, "Role of complexes formation between drugs and penetration enhancers in transdermal delivery" in International Journal of Pharmaceutics, 363, no. 1-2 (2008):40-49,
https://doi.org/10.1016/j.ijpharm.2008.06.032 . .

TY  - JOUR
AU  - Dilber, Sanda
AU  - Dobrić, Silva
AU  - Juranić, Zorica
AU  - Marković, Bojan
AU  - Vladimirov, Sote
AU  - Juranić, Ivan O.
PY  - 2008
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1101
AB  - The article describes a two-step synthesis of diastereomeric 3-hydroxy-2methyl-3-( 4-biphenylyl) butanoic acids. In the first step an intermediate alpha-bromo propanoic acid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatsky reaction in presence of Zn in tetrahydrofuran (THF) at -5 to 10 C between the previously synthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied beta-hydroxy- beta-arylpropanoic acids has already been reported. These beta-hydroxy-beta-arylpropanoic acids belong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDs such as ibuprofen. The anti-inflammatory activity and gastric tolerability of the synthesized compounds were evaluated. Molecular docking experiments were carried out to identify potential COX-2 inhibitors among the beta-hydroxy- beta-aryl-alkanoic acids class. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration and that the compounds 2-(9-( 9-hydroxy-fluorenyl))-2-methylpropanoic acid ( 5) and 3-hydroxy-3,3-diphenyl- propanoic acid (3) possess the strongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID, and that none of tested substances or ibuprofen produced any significant gastric lesions.
PB  - Molecular Diversity Preservation Int, Basel
T2  - Molecules
T1  - Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids
VL  - 13
IS  - 3
SP  - 603
EP  - 615
DO  - 10.3390/molecules13030603
ER  - 

@article{
author = "Dilber, Sanda and Dobrić, Silva and Juranić, Zorica and Marković, Bojan and Vladimirov, Sote and Juranić, Ivan O.",
year = "2008",
abstract = "The article describes a two-step synthesis of diastereomeric 3-hydroxy-2methyl-3-( 4-biphenylyl) butanoic acids. In the first step an intermediate alpha-bromo propanoic acid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatsky reaction in presence of Zn in tetrahydrofuran (THF) at -5 to 10 C between the previously synthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied beta-hydroxy- beta-arylpropanoic acids has already been reported. These beta-hydroxy-beta-arylpropanoic acids belong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDs such as ibuprofen. The anti-inflammatory activity and gastric tolerability of the synthesized compounds were evaluated. Molecular docking experiments were carried out to identify potential COX-2 inhibitors among the beta-hydroxy- beta-aryl-alkanoic acids class. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration and that the compounds 2-(9-( 9-hydroxy-fluorenyl))-2-methylpropanoic acid ( 5) and 3-hydroxy-3,3-diphenyl- propanoic acid (3) possess the strongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID, and that none of tested substances or ibuprofen produced any significant gastric lesions.",
publisher = "Molecular Diversity Preservation Int, Basel",
journal = "Molecules",
title = "Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids",
volume = "13",
number = "3",
pages = "603-615",
doi = "10.3390/molecules13030603"
}

Dilber, S., Dobrić, S., Juranić, Z., Marković, B., Vladimirov, S.,& Juranić, I. O.. (2008). Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids. in Molecules
Molecular Diversity Preservation Int, Basel., 13(3), 603-615.
https://doi.org/10.3390/molecules13030603

Dilber S, Dobrić S, Juranić Z, Marković B, Vladimirov S, Juranić IO. Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids. in Molecules. 2008;13(3):603-615.
doi:10.3390/molecules13030603 .

Dilber, Sanda, Dobrić, Silva, Juranić, Zorica, Marković, Bojan, Vladimirov, Sote, Juranić, Ivan O., "Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids" in Molecules, 13, no. 3 (2008):603-615,
https://doi.org/10.3390/molecules13030603 . .

TY  - JOUR
AU  - Verbić, Tatjana Ž.
AU  - Drakulić, Branko
AU  - Zloh, Mire
AU  - Pecelj, Jovana R.
AU  - Popović, Gordana
AU  - Juranić, Ivan O.
PY  - 2007
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/997
AB  - The protolytic equilibria of 13 4-aryl-2,4-dioxobutanoic acids (ADKs) were spectrophotometrically studied in aqueous solutions in the pH range 1-9 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl), with the exception of the 4-OH-derivative which was also potentiometrically studied in the pH range 7-10 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl). In solution, the compounds simultaneously exist in one diketo and two enolic forms; therefore, the determined acidity constants (pKa1 1.87-2.29, pKa2 6.63-8.13 and pKa3(4-OH-) 9.52) represent system macro constants. The 1H-NMR spectrum of the parent compound (4-phenyl- -2,4-dioxobutanoic acid) (25 °C, pD 5.0) proved the existence of all tautomeric forms. Using the extended Hammett relation, the determined pKa values were correlated with literature σ values. The predicted pKa values were in fair accordance with the experimentally observed ones. Molecular, monoanionic and dianionic forms of the parent compound were optimized by the semi-empirical molecular orbital PM6 method using the implicit water solvation model (COSMO). The obtained geometries were used to explain the quality of the LFER models.
AB  - Protolitičke ravnoteže 13 jedinjenja iz klase 4-aril-2,4-dioksobutanskih kiselina (ADK) spektrofotometrijski su proučavane u vodenim rastvorima u pH intervalu 1-9 pri temperaturi 25±1 °C i jonskoj jačini rastvora 0.1 mol l-1 (NaCl), sa izuzetkom 4-OH-derivata koji je proučavan i potenciometrijski u pH intervalu 7-10 pri istim uslovima. Kako ADK u vodenom rastvoru podležu keto-enolnoj tautomeriji i istovremeno postoje u diketo i dva enolna oblika, to određene kiselinske konstante (pKa1 1.87-2.29, pKa2 6.63-8.13 i pKa3(4-OH-) 9.52) predstavljaju makro konstante za dati sistem. 1H-NMR spektar osnovne supstance (4-fenil-2,4-dioksobutanska kiselina) (25 °C, pD 5.0) potvrđuje prisustvo svih tautomernih oblika. Upotrebom proširene Hametove korelacije, određene pKa vrednosti korelisane su sa literaturnim σ vrednostima. Predviđene pKa vrednosti dobro se slažu sa eksperimentalno dobijenim. Molekulski, monoanjonski i dianjonski oblici osnovne supstance su optimizovani semiempirijskom molekulsko-orbitalnom PM6 metodom sa implicitnim modelom solvatacije u vodi (COSMO). Dobijene geometrije su upotrebljene za objašnjenje kvaliteta LFER modela.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions
T1  - Linearne korelacije slobodne energije (LFER) protolitičkih ravnoteža 4-aril-2,4-dioksobutanskih kiselina u vodenim rastvorima
VL  - 72
IS  - 12
SP  - 1201
EP  - 1216
DO  - 10.2298/JSC0712201V
ER  - 

@article{
author = "Verbić, Tatjana Ž. and Drakulić, Branko and Zloh, Mire and Pecelj, Jovana R. and Popović, Gordana and Juranić, Ivan O.",
year = "2007",
abstract = "The protolytic equilibria of 13 4-aryl-2,4-dioxobutanoic acids (ADKs) were spectrophotometrically studied in aqueous solutions in the pH range 1-9 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl), with the exception of the 4-OH-derivative which was also potentiometrically studied in the pH range 7-10 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl). In solution, the compounds simultaneously exist in one diketo and two enolic forms; therefore, the determined acidity constants (pKa1 1.87-2.29, pKa2 6.63-8.13 and pKa3(4-OH-) 9.52) represent system macro constants. The 1H-NMR spectrum of the parent compound (4-phenyl- -2,4-dioxobutanoic acid) (25 °C, pD 5.0) proved the existence of all tautomeric forms. Using the extended Hammett relation, the determined pKa values were correlated with literature σ values. The predicted pKa values were in fair accordance with the experimentally observed ones. Molecular, monoanionic and dianionic forms of the parent compound were optimized by the semi-empirical molecular orbital PM6 method using the implicit water solvation model (COSMO). The obtained geometries were used to explain the quality of the LFER models., Protolitičke ravnoteže 13 jedinjenja iz klase 4-aril-2,4-dioksobutanskih kiselina (ADK) spektrofotometrijski su proučavane u vodenim rastvorima u pH intervalu 1-9 pri temperaturi 25±1 °C i jonskoj jačini rastvora 0.1 mol l-1 (NaCl), sa izuzetkom 4-OH-derivata koji je proučavan i potenciometrijski u pH intervalu 7-10 pri istim uslovima. Kako ADK u vodenom rastvoru podležu keto-enolnoj tautomeriji i istovremeno postoje u diketo i dva enolna oblika, to određene kiselinske konstante (pKa1 1.87-2.29, pKa2 6.63-8.13 i pKa3(4-OH-) 9.52) predstavljaju makro konstante za dati sistem. 1H-NMR spektar osnovne supstance (4-fenil-2,4-dioksobutanska kiselina) (25 °C, pD 5.0) potvrđuje prisustvo svih tautomernih oblika. Upotrebom proširene Hametove korelacije, određene pKa vrednosti korelisane su sa literaturnim σ vrednostima. Predviđene pKa vrednosti dobro se slažu sa eksperimentalno dobijenim. Molekulski, monoanjonski i dianjonski oblici osnovne supstance su optimizovani semiempirijskom molekulsko-orbitalnom PM6 metodom sa implicitnim modelom solvatacije u vodi (COSMO). Dobijene geometrije su upotrebljene za objašnjenje kvaliteta LFER modela.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions, Linearne korelacije slobodne energije (LFER) protolitičkih ravnoteža 4-aril-2,4-dioksobutanskih kiselina u vodenim rastvorima",
volume = "72",
number = "12",
pages = "1201-1216",
doi = "10.2298/JSC0712201V"
}

Verbić, T. Ž., Drakulić, B., Zloh, M., Pecelj, J. R., Popović, G.,& Juranić, I. O.. (2007). An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 72(12), 1201-1216.
https://doi.org/10.2298/JSC0712201V

Verbić TŽ, Drakulić B, Zloh M, Pecelj JR, Popović G, Juranić IO. An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions. in Journal of the Serbian Chemical Society. 2007;72(12):1201-1216.
doi:10.2298/JSC0712201V .

Verbić, Tatjana Ž., Drakulić, Branko, Zloh, Mire, Pecelj, Jovana R., Popović, Gordana, Juranić, Ivan O., "An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1201-1216,
https://doi.org/10.2298/JSC0712201V . .

TY  - JOUR
AU  - Pfendt, Lidija
AU  - Dražić, Branka
AU  - Popović, Gordana
AU  - Drakulić, Branko
AU  - Vitnik, Željko J.
AU  - Juranić, Ivan O.
PY  - 2003
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/457
AB  - For a series of seven unsaturated and seven epoxy di- and tricarboxylic acids, pK(a)(a) values were determined potentiometrically in aqueous media at 25 degreesC and an ionic strength of 0.1 M (NaCl). The thermodynamic pKaa values were correlated with the atomic charges of carboxylic group calculated by the MNDO-PM3 semiempirical MO method.
PB  - Scientific Reviews Ltd.
T2  - Journal of Chemical Research - Part S
T1  - Determination of all pK(a) values of some di- and tri-carboxylic unsaturated and epoxy acids and their polylinear correlation with the carboxylic group atomic charges
IS  - 5
SP  - 247
EP  - 248
UR  - https://hdl.handle.net/21.15107/rcub_farfar_457
ER  - 

@article{
author = "Pfendt, Lidija and Dražić, Branka and Popović, Gordana and Drakulić, Branko and Vitnik, Željko J. and Juranić, Ivan O.",
year = "2003",
abstract = "For a series of seven unsaturated and seven epoxy di- and tricarboxylic acids, pK(a)(a) values were determined potentiometrically in aqueous media at 25 degreesC and an ionic strength of 0.1 M (NaCl). The thermodynamic pKaa values were correlated with the atomic charges of carboxylic group calculated by the MNDO-PM3 semiempirical MO method.",
publisher = "Scientific Reviews Ltd.",
journal = "Journal of Chemical Research - Part S",
title = "Determination of all pK(a) values of some di- and tri-carboxylic unsaturated and epoxy acids and their polylinear correlation with the carboxylic group atomic charges",
number = "5",
pages = "247-248",
url = "https://hdl.handle.net/21.15107/rcub_farfar_457"
}

Pfendt, L., Dražić, B., Popović, G., Drakulić, B., Vitnik, Ž. J.,& Juranić, I. O.. (2003). Determination of all pK(a) values of some di- and tri-carboxylic unsaturated and epoxy acids and their polylinear correlation with the carboxylic group atomic charges. in Journal of Chemical Research - Part S
Scientific Reviews Ltd..(5), 247-248.
https://hdl.handle.net/21.15107/rcub_farfar_457

Pfendt L, Dražić B, Popović G, Drakulić B, Vitnik ŽJ, Juranić IO. Determination of all pK(a) values of some di- and tri-carboxylic unsaturated and epoxy acids and their polylinear correlation with the carboxylic group atomic charges. in Journal of Chemical Research - Part S. 2003;(5):247-248.
https://hdl.handle.net/21.15107/rcub_farfar_457 .

Pfendt, Lidija, Dražić, Branka, Popović, Gordana, Drakulić, Branko, Vitnik, Željko J., Juranić, Ivan O., "Determination of all pK(a) values of some di- and tri-carboxylic unsaturated and epoxy acids and their polylinear correlation with the carboxylic group atomic charges" in Journal of Chemical Research - Part S, no. 5 (2003):247-248,
https://hdl.handle.net/21.15107/rcub_farfar_457 .

TY  - JOUR
AU  - Pfendt, Lidija
AU  - Popović, Gordana
AU  - Kostić, M.
AU  - Stevović, Lj.
AU  - Drakulić, Branko
AU  - Juranić, Ivan O.
PY  - 2000
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/269
AB  - The pKa values for a series of eight p-substituted trans-2,3-epoxy-4-phenyl butanoic acids (p-substituted trans-β-aroylepoxyacrylic acids) have been determined potentiometrically in aqueous media at 25 °C at an ionic strength of 0.1 mol/dm3 (NaCl). The transmission of polar effects from the substituents on the phenyl nucleus to the carboxylic group through the side chain involving a carbonyl group and an epoxide ring was investigated. The pKa values were correlated with structure using the Hammett, Taft and Yukawa-Tsuno approaches. The Hammett ρ constant (0.34) was compared with analogue values for structurally similar acids.
AB  - Određene su pKa vrednosti za seriju od osam p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina (p-supstituisanih trans-β-aroilepoksiakrilnih kiselina). Vrednosti su određene potenciometrijski u vodenoj sredini na 25 °C i jonskoj sili 0.1 mol/dm3 (NaCl). Proučavan je prenos polarnih efekata sa supstituenata na fenil jezgru ka karboksilnoj grupi kroz bočni niz koji sadrži karbonilnu grupu i epoksidni prsten. pKa vrednosti su korelisane sa strukturom primenom Hammett-ovog, Taft-ovog i Yukawa-Tsuno-ovog pristupa. Hammett-ova ρ konstanta (0,34) je upoređena sa analognim vrednostima za strukturno slične kiseline.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids
T1  - Određivanje pKa vrednosti i korelacija sa strukturom p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina
VL  - 65
IS  - 11
SP  - 781
EP  - 788
UR  - https://hdl.handle.net/21.15107/rcub_farfar_269
ER  - 

@article{
author = "Pfendt, Lidija and Popović, Gordana and Kostić, M. and Stevović, Lj. and Drakulić, Branko and Juranić, Ivan O.",
year = "2000",
abstract = "The pKa values for a series of eight p-substituted trans-2,3-epoxy-4-phenyl butanoic acids (p-substituted trans-β-aroylepoxyacrylic acids) have been determined potentiometrically in aqueous media at 25 °C at an ionic strength of 0.1 mol/dm3 (NaCl). The transmission of polar effects from the substituents on the phenyl nucleus to the carboxylic group through the side chain involving a carbonyl group and an epoxide ring was investigated. The pKa values were correlated with structure using the Hammett, Taft and Yukawa-Tsuno approaches. The Hammett ρ constant (0.34) was compared with analogue values for structurally similar acids., Određene su pKa vrednosti za seriju od osam p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina (p-supstituisanih trans-β-aroilepoksiakrilnih kiselina). Vrednosti su određene potenciometrijski u vodenoj sredini na 25 °C i jonskoj sili 0.1 mol/dm3 (NaCl). Proučavan je prenos polarnih efekata sa supstituenata na fenil jezgru ka karboksilnoj grupi kroz bočni niz koji sadrži karbonilnu grupu i epoksidni prsten. pKa vrednosti su korelisane sa strukturom primenom Hammett-ovog, Taft-ovog i Yukawa-Tsuno-ovog pristupa. Hammett-ova ρ konstanta (0,34) je upoređena sa analognim vrednostima za strukturno slične kiseline.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids, Određivanje pKa vrednosti i korelacija sa strukturom p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina",
volume = "65",
number = "11",
pages = "781-788",
url = "https://hdl.handle.net/21.15107/rcub_farfar_269"
}

Pfendt, L., Popović, G., Kostić, M., Stevović, Lj., Drakulić, B.,& Juranić, I. O.. (2000). Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 65(11), 781-788.
https://hdl.handle.net/21.15107/rcub_farfar_269

Pfendt L, Popović G, Kostić M, Stevović L, Drakulić B, Juranić IO. Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids. in Journal of the Serbian Chemical Society. 2000;65(11):781-788.
https://hdl.handle.net/21.15107/rcub_farfar_269 .

Pfendt, Lidija, Popović, Gordana, Kostić, M., Stevović, Lj., Drakulić, Branko, Juranić, Ivan O., "Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):781-788,
https://hdl.handle.net/21.15107/rcub_farfar_269 .