TY  - JOUR
AU  - Popović-Nikolić, Marija
AU  - Čakar, Mira
AU  - Todorović, Nina
AU  - Nikolić, Katarina
AU  - Popović, Gordana
PY  - 2024
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5589
AB  - The acid–base equilibria of raloxifene and the mutual influence of pH and solubility enhancers on the solubility of raloxifene
hydrochloride were studied. The apparent ionization constants (pKa*) of raloxifene were determined potentiometrically in
methanol–water mixtures (45%-55% w/w), and the pKa values (pKa1 = 7.21 ± 0.02, pKa2 = 7.86 ± 0.02, pKa3 = 9.97 ± 0.04)
defining ionization in aqueous media were obtained by extrapolating the pKa* values to 0% of methanol. The obtained pKa
values were assigned to the corresponding ionization centers. Based on the ionization constants obtained in this study, the
distribution of the equilibrium forms of raloxifene was calculated. The solubility of raloxifene hydrochloride in 0.01 M
HCl, acetate buffer pH 4.5 and phosphate buffer pH 6.8 was studied with and without the presence of β-CD, HP-β-CD and
polysorbate 80. The most effective solubility enhancer of raloxifene hydrochloride in 0.01 M HCl was polysorbate 80 at a
concentration of 0.5%, while the influence of this enhancer in phosphate buffer pH 6.8 was negligible. The highest solubility
of raloxifene hydrochloride in acetate and phosphate buffer was achieved in the presence of 10–
3 M HP–β-CD which
was 1.3-fold higher in both 0.01 M HCl and acetate buffer and 2.3-fold higher in phosphate buffer than in the presence of
10–
3 M β-CD.
PB  - Springer Nature
T2  - Chemical Papers
T1  - Study on protolytic equilibria and the effects of pH, cyclodextrins and polysorbate 80 on solubility of raloxifene hydrochloride
DO  - 10.1007/s11696-024-03399-1
ER  - 

@article{
author = "Popović-Nikolić, Marija and Čakar, Mira and Todorović, Nina and Nikolić, Katarina and Popović, Gordana",
year = "2024",
abstract = "The acid–base equilibria of raloxifene and the mutual influence of pH and solubility enhancers on the solubility of raloxifene
hydrochloride were studied. The apparent ionization constants (pKa*) of raloxifene were determined potentiometrically in
methanol–water mixtures (45%-55% w/w), and the pKa values (pKa1 = 7.21 ± 0.02, pKa2 = 7.86 ± 0.02, pKa3 = 9.97 ± 0.04)
defining ionization in aqueous media were obtained by extrapolating the pKa* values to 0% of methanol. The obtained pKa
values were assigned to the corresponding ionization centers. Based on the ionization constants obtained in this study, the
distribution of the equilibrium forms of raloxifene was calculated. The solubility of raloxifene hydrochloride in 0.01 M
HCl, acetate buffer pH 4.5 and phosphate buffer pH 6.8 was studied with and without the presence of β-CD, HP-β-CD and
polysorbate 80. The most effective solubility enhancer of raloxifene hydrochloride in 0.01 M HCl was polysorbate 80 at a
concentration of 0.5%, while the influence of this enhancer in phosphate buffer pH 6.8 was negligible. The highest solubility
of raloxifene hydrochloride in acetate and phosphate buffer was achieved in the presence of 10–
3 M HP–β-CD which
was 1.3-fold higher in both 0.01 M HCl and acetate buffer and 2.3-fold higher in phosphate buffer than in the presence of
10–
3 M β-CD.",
publisher = "Springer Nature",
journal = "Chemical Papers",
title = "Study on protolytic equilibria and the effects of pH, cyclodextrins and polysorbate 80 on solubility of raloxifene hydrochloride",
doi = "10.1007/s11696-024-03399-1"
}

Popović-Nikolić, M., Čakar, M., Todorović, N., Nikolić, K.,& Popović, G.. (2024). Study on protolytic equilibria and the effects of pH, cyclodextrins and polysorbate 80 on solubility of raloxifene hydrochloride. in Chemical Papers
Springer Nature..
https://doi.org/10.1007/s11696-024-03399-1

Popović-Nikolić M, Čakar M, Todorović N, Nikolić K, Popović G. Study on protolytic equilibria and the effects of pH, cyclodextrins and polysorbate 80 on solubility of raloxifene hydrochloride. in Chemical Papers. 2024;.
doi:10.1007/s11696-024-03399-1 .

Popović-Nikolić, Marija, Čakar, Mira, Todorović, Nina, Nikolić, Katarina, Popović, Gordana, "Study on protolytic equilibria and the effects of pH, cyclodextrins and polysorbate 80 on solubility of raloxifene hydrochloride" in Chemical Papers (2024),
https://doi.org/10.1007/s11696-024-03399-1 . .

TY  - JOUR
AU  - Tasić, Gordana
AU  - Maslak, Veselin
AU  - Husinec, Suren
AU  - Todorović, Nina
AU  - Savić, Vladimir
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2375
AB  - The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine
VL  - 56
IS  - 19
SP  - 2529
EP  - 2532
DO  - 10.1016/j.tetlet.2015.03.129
ER  - 

@article{
author = "Tasić, Gordana and Maslak, Veselin and Husinec, Suren and Todorović, Nina and Savić, Vladimir",
year = "2015",
abstract = "The intramolecular Heck reaction has been examined for the preparation of the core bicyclic structure of corialstonidine. Initial attempts to cyclise a vinyl iodide moiety onto a cyclic allyl alcohol were complicated by various side reactions. However, the corresponding process performed under reductive conditions on a conjugated ketone, obtained from the cyclic allyl alcohol, afforded the desired bicyclo[3.2.1] derivative. This compound possesses the skeletal features of the carbocyclic fragment of corialstonidine and is suitable for further transformations aimed towards the synthesis of the natural product or its derivatives.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine",
volume = "56",
number = "19",
pages = "2529-2532",
doi = "10.1016/j.tetlet.2015.03.129"
}

Tasić, G., Maslak, V., Husinec, S., Todorović, N.,& Savić, V.. (2015). Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 56(19), 2529-2532.
https://doi.org/10.1016/j.tetlet.2015.03.129

Tasić G, Maslak V, Husinec S, Todorović N, Savić V. Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine. in Tetrahedron-Asymmetry. 2015;56(19):2529-2532.
doi:10.1016/j.tetlet.2015.03.129 .

Tasić, Gordana, Maslak, Veselin, Husinec, Suren, Todorović, Nina, Savić, Vladimir, "Study of the intramolecular Heck reaction: synthesis of the bicyclic core of corialstonidine" in Tetrahedron-Asymmetry, 56, no. 19 (2015):2529-2532,
https://doi.org/10.1016/j.tetlet.2015.03.129 . .

TY  - JOUR
AU  - Marković, Violeta
AU  - Erić, Slavica
AU  - Stanojković, Tatjana
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Manojlović, Nedeljko
AU  - Jelić, Ratomir
AU  - Joksović, Milan D.
PY  - 2011
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1555
AB  - Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones
VL  - 21
IS  - 15
SP  - 4416
EP  - 4421
DO  - 10.1016/j.bmcl.2011.06.025
ER  - 

@article{
author = "Marković, Violeta and Erić, Slavica and Stanojković, Tatjana and Gligorijević, Nevenka and Aranđelović, Sandra and Todorović, Nina and Trifunović, Snežana and Manojlović, Nedeljko and Jelić, Ratomir and Joksović, Milan D.",
year = "2011",
abstract = "Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones",
volume = "21",
number = "15",
pages = "4416-4421",
doi = "10.1016/j.bmcl.2011.06.025"
}

Marković, V., Erić, S., Stanojković, T., Gligorijević, N., Aranđelović, S., Todorović, N., Trifunović, S., Manojlović, N., Jelić, R.,& Joksović, M. D.. (2011). Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones. in Bioorganic & Medicinal Chemistry Letters
Pergamon-Elsevier Science Ltd, Oxford., 21(15), 4416-4421.
https://doi.org/10.1016/j.bmcl.2011.06.025

Marković V, Erić S, Stanojković T, Gligorijević N, Aranđelović S, Todorović N, Trifunović S, Manojlović N, Jelić R, Joksović MD. Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones. in Bioorganic & Medicinal Chemistry Letters. 2011;21(15):4416-4421.
doi:10.1016/j.bmcl.2011.06.025 .

Marković, Violeta, Erić, Slavica, Stanojković, Tatjana, Gligorijević, Nevenka, Aranđelović, Sandra, Todorović, Nina, Trifunović, Snežana, Manojlović, Nedeljko, Jelić, Ratomir, Joksović, Milan D., "Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones" in Bioorganic & Medicinal Chemistry Letters, 21, no. 15 (2011):4416-4421,
https://doi.org/10.1016/j.bmcl.2011.06.025 . .

TY  - JOUR
AU  - Husinec, Suren
AU  - Jadranin, Milka
AU  - Marković, Rade
AU  - Petković, Miloš
AU  - Savić, Vladimir
AU  - Todorović, Nina
PY  - 2010
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1382
AB  - Allyl acetates were synthesised from allenes utilising methodology based on the general reactivity of pi-allyl palladium intermediates which participate efficiently in transformations involving nucleophiles. Reactions of allenes and aryl iodides in the presence of AcONa and Pd(OAc)(2)/PPh(3) as the catalytic system afforded allyl acetates in moderate to good yields. Monosubstituted allenes, depending on their structure, produced either a separable mixture of two regioisomeric products or a single regioisomer. As allylic acetates can be easily hydrolysed, the methodology is applicable for the synthesis of allyl alcohols as well.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron-Asymmetry
T1  - Palladium-catalysed synthesis of allyl acetates from allenes
VL  - 51
IS  - 31
SP  - 4066
EP  - 4068
DO  - 10.1016/j.tetlet.2010.05.136
ER  - 

@article{
author = "Husinec, Suren and Jadranin, Milka and Marković, Rade and Petković, Miloš and Savić, Vladimir and Todorović, Nina",
year = "2010",
abstract = "Allyl acetates were synthesised from allenes utilising methodology based on the general reactivity of pi-allyl palladium intermediates which participate efficiently in transformations involving nucleophiles. Reactions of allenes and aryl iodides in the presence of AcONa and Pd(OAc)(2)/PPh(3) as the catalytic system afforded allyl acetates in moderate to good yields. Monosubstituted allenes, depending on their structure, produced either a separable mixture of two regioisomeric products or a single regioisomer. As allylic acetates can be easily hydrolysed, the methodology is applicable for the synthesis of allyl alcohols as well.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron-Asymmetry",
title = "Palladium-catalysed synthesis of allyl acetates from allenes",
volume = "51",
number = "31",
pages = "4066-4068",
doi = "10.1016/j.tetlet.2010.05.136"
}

Husinec, S., Jadranin, M., Marković, R., Petković, M., Savić, V.,& Todorović, N.. (2010). Palladium-catalysed synthesis of allyl acetates from allenes. in Tetrahedron-Asymmetry
Pergamon-Elsevier Science Ltd, Oxford., 51(31), 4066-4068.
https://doi.org/10.1016/j.tetlet.2010.05.136

Husinec S, Jadranin M, Marković R, Petković M, Savić V, Todorović N. Palladium-catalysed synthesis of allyl acetates from allenes. in Tetrahedron-Asymmetry. 2010;51(31):4066-4068.
doi:10.1016/j.tetlet.2010.05.136 .

Husinec, Suren, Jadranin, Milka, Marković, Rade, Petković, Miloš, Savić, Vladimir, Todorović, Nina, "Palladium-catalysed synthesis of allyl acetates from allenes" in Tetrahedron-Asymmetry, 51, no. 31 (2010):4066-4068,
https://doi.org/10.1016/j.tetlet.2010.05.136 . .