TY  - JOUR
AU  - Šegan, Sandra
AU  - Bozinovic, Nina
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2243
AB  - Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Journal of Separation Science
T1  - Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs
VL  - 40
IS  - 10
SP  - 2089
EP  - 2096
DO  - 10.1002/jssc.201601442
ER  - 

@article{
author = "Šegan, Sandra and Bozinovic, Nina and Opsenica, Igor and Andrić, Filip",
year = "2017",
abstract = "Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Journal of Separation Science",
title = "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs",
volume = "40",
number = "10",
pages = "2089-2096",
doi = "10.1002/jssc.201601442"
}

Šegan, S., Bozinovic, N., Opsenica, I.,& Andrić, F.. (2017). Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 40(10), 2089-2096.
https://doi.org/10.1002/jssc.201601442

Šegan S, Bozinovic N, Opsenica I, Andrić F. Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science. 2017;40(10):2089-2096.
doi:10.1002/jssc.201601442 .

Šegan, Sandra, Bozinovic, Nina, Opsenica, Igor, Andrić, Filip, "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs" in Journal of Separation Science, 40, no. 10 (2017):2089-2096,
https://doi.org/10.1002/jssc.201601442 . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Bozinovic, Nina
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2982
AB  - Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Journal of Separation Science
T1  - Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs
VL  - 40
IS  - 10
SP  - 2089
EP  - 2096
DO  - 10.1002/jssc.201601442
ER  - 

@article{
author = "Šegan, Sandra and Bozinovic, Nina and Opsenica, Igor and Andrić, Filip",
year = "2017",
abstract = "Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Journal of Separation Science",
title = "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs",
volume = "40",
number = "10",
pages = "2089-2096",
doi = "10.1002/jssc.201601442"
}

Šegan, S., Bozinovic, N., Opsenica, I.,& Andrić, F.. (2017). Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 40(10), 2089-2096.
https://doi.org/10.1002/jssc.201601442

Šegan S, Bozinovic N, Opsenica I, Andrić F. Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science. 2017;40(10):2089-2096.
doi:10.1002/jssc.201601442 .

Šegan, Sandra, Bozinovic, Nina, Opsenica, Igor, Andrić, Filip, "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs" in Journal of Separation Science, 40, no. 10 (2017):2089-2096,
https://doi.org/10.1002/jssc.201601442 . .

TY  - JOUR
AU  - Bozinovic, Nina
AU  - Šegan, Sandra
AU  - Vojnovic, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1887
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 

@article{
author = "Bozinovic, Nina and Šegan, Sandra and Vojnovic, Sandra and Pavić, Aleksandar and Šolaja, Bogdan and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}

Bozinovic, N., Šegan, S., Vojnovic, S., Pavić, A., Šolaja, B., Nikodinović-Runić, J.,& Opsenica, I.. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809

Bozinovic N, Šegan S, Vojnovic S, Pavić A, Šolaja B, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design. 2016;88(6):795-806.
doi:10.1111/cbdd.12809 .

Bozinovic, Nina, Šegan, Sandra, Vojnovic, Sandra, Pavić, Aleksandar, Šolaja, Bogdan, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" in Chemical Biology & Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 . .

TY  - JOUR
AU  - Bozinovic, Nina
AU  - Šegan, Sandra
AU  - Vojnovic, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3192
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 

@article{
author = "Bozinovic, Nina and Šegan, Sandra and Vojnovic, Sandra and Pavić, Aleksandar and Šolaja, Bogdan and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}

Bozinovic, N., Šegan, S., Vojnovic, S., Pavić, A., Šolaja, B., Nikodinović-Runić, J.,& Opsenica, I.. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809

Bozinovic N, Šegan S, Vojnovic S, Pavić A, Šolaja B, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design. 2016;88(6):795-806.
doi:10.1111/cbdd.12809 .

Bozinovic, Nina, Šegan, Sandra, Vojnovic, Sandra, Pavić, Aleksandar, Šolaja, Bogdan, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" in Chemical Biology & Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 . .

TY  - JOUR
AU  - Bozinovic, Nina
AU  - Novaković, Irena
AU  - Kostić Rajačić, Slađana
AU  - Opsenica, Igor
AU  - Šolaja, Bogdan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1702
AB  - A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39-78 mu g mL(-1)), while azepine 12 showed promising antifungal activity (MIC ranged 156-313 mu g mL(-1)). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and antimicrobial activity of azepine and thiepine derivatives
VL  - 80
IS  - 7
SP  - 839
EP  - 852
DO  - 10.2298/JSC150116013B
ER  - 

@article{
author = "Bozinovic, Nina and Novaković, Irena and Kostić Rajačić, Slađana and Opsenica, Igor and Šolaja, Bogdan",
year = "2015",
abstract = "A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39-78 mu g mL(-1)), while azepine 12 showed promising antifungal activity (MIC ranged 156-313 mu g mL(-1)). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and antimicrobial activity of azepine and thiepine derivatives",
volume = "80",
number = "7",
pages = "839-852",
doi = "10.2298/JSC150116013B"
}

Bozinovic, N., Novaković, I., Kostić Rajačić, S., Opsenica, I.,& Šolaja, B.. (2015). Synthesis and antimicrobial activity of azepine and thiepine derivatives. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 80(7), 839-852.
https://doi.org/10.2298/JSC150116013B

Bozinovic N, Novaković I, Kostić Rajačić S, Opsenica I, Šolaja B. Synthesis and antimicrobial activity of azepine and thiepine derivatives. in Journal of the Serbian Chemical Society. 2015;80(7):839-852.
doi:10.2298/JSC150116013B .

Bozinovic, Nina, Novaković, Irena, Kostić Rajačić, Slađana, Opsenica, Igor, Šolaja, Bogdan, "Synthesis and antimicrobial activity of azepine and thiepine derivatives" in Journal of the Serbian Chemical Society, 80, no. 7 (2015):839-852,
https://doi.org/10.2298/JSC150116013B . .