TY  - JOUR
AU  - Božić, Bojan
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Rančić, Milica
AU  - Trisović, Nemanja
AU  - Božić, Biljana
AU  - Ušćumlić, Gordana
PY  - 2017
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/880
AB  - A series of six novel 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acids and six corresponding methyl esters were synthesized. All compounds were characterized by melting points, elemental analysis, FT-IR, H-1 and C-13 NMR spectroscopy. Crystal structure of methyl-2-(5-(4-methoxybenzylidene)-2,4-dioxotetrahydrothiazole-3-yl) propionate was confirmed by X-ray analysis. The antiproliferative activity of all synthesized compounds against human colon cancer, breast cancer and myelogenous leukemia cell lines, i.e. HCT-116, MDA-231 and K562, respectively, was evaluated. The results indicate that antiproliferative activity of the synthesized esters is better than the activity of the corresponding acids. All synthesized compounds showed significant antiproliferative effects against HCT116 cells in all tested concentrations (0.01-100 lM). Moreover, in vitro antimicrobial activity against a wide range of tested microorganisms was examined.
T2  - Arabian Journal of Chemistry
T1  - Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives
EP  - S2643
SP  - S2637
VL  - 10
DO  - 10.1016/j.arabjc.2013.10.002
UR  - conv_1316
ER  - 

@article{
author = "Božić, Bojan and Rogan, Jelena and Poleti, Dejan and Rančić, Milica and Trisović, Nemanja and Božić, Biljana and Ušćumlić, Gordana",
year = "2017",
abstract = "A series of six novel 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acids and six corresponding methyl esters were synthesized. All compounds were characterized by melting points, elemental analysis, FT-IR, H-1 and C-13 NMR spectroscopy. Crystal structure of methyl-2-(5-(4-methoxybenzylidene)-2,4-dioxotetrahydrothiazole-3-yl) propionate was confirmed by X-ray analysis. The antiproliferative activity of all synthesized compounds against human colon cancer, breast cancer and myelogenous leukemia cell lines, i.e. HCT-116, MDA-231 and K562, respectively, was evaluated. The results indicate that antiproliferative activity of the synthesized esters is better than the activity of the corresponding acids. All synthesized compounds showed significant antiproliferative effects against HCT116 cells in all tested concentrations (0.01-100 lM). Moreover, in vitro antimicrobial activity against a wide range of tested microorganisms was examined.",
journal = "Arabian Journal of Chemistry",
title = "Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives",
pages = "S2643-S2637",
volume = "10",
doi = "10.1016/j.arabjc.2013.10.002",
url = "conv_1316"
}

Božić, B., Rogan, J., Poleti, D., Rančić, M., Trisović, N., Božić, B.,& Ušćumlić, G.. (2017). Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives. in Arabian Journal of Chemistry, 10, S2637-S2643.
https://doi.org/10.1016/j.arabjc.2013.10.002
conv_1316

Božić B, Rogan J, Poleti D, Rančić M, Trisović N, Božić B, Ušćumlić G. Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives. in Arabian Journal of Chemistry. 2017;10:S2637-S2643.
doi:10.1016/j.arabjc.2013.10.002
conv_1316 .

Božić, Bojan, Rogan, Jelena, Poleti, Dejan, Rančić, Milica, Trisović, Nemanja, Božić, Biljana, Ušćumlić, Gordana, "Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl) propanoic acid derivatives" in Arabian Journal of Chemistry, 10 (2017):S2637-S2643,
https://doi.org/10.1016/j.arabjc.2013.10.002 .,
conv_1316 .

TY  - JOUR
AU  - Rančić, Milica
AU  - Trisović, Nemanja
AU  - Milcić, Miloš
AU  - Jovanović, Maja
AU  - Jovanović, Bratislav
AU  - Marinković, Aleksandar
PY  - 2014
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/577
AB  - Two series of 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines have been synthesized using different methods of conventional and microwave-assisted synthesis, and linear free-energy relationships have been applied to the C-13 NMR chemical shifts of the carbon atoms of interest. The substituent-induced chemical shifts have been analyzed using single substituent parameter and dual substituent parameter methods. The presented correlations describe satisfactorily the field and resonance substituent effects having similar contributions for C1 and the azomethine carbon, with exception of the carbon atom in para position to the substituent X. In both series, negative values have been found for C1 atom (reverse substituent effect). Quantum chemical calculations of the optimized geometries at MP2/6-31G++(d,p) level, together with C-13 NMR chemical shifts, give a better insight into the influence of the molecular conformation on the transmission of electronic substituent effects. The comparison of correlation results for different series of imines with phenyl, 4-nitrophenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl group attached at the azomethine carbon with the results for 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines for the same substituent set (X) indicates that a combination of the influences of electronic effects of the substituent X and the (1)-unit can be described as a sensitive balance of different resonance structures.
T2  - Journal of Heterocyclic Chemistry
T1  - Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines
EP  - 1451
IS  - 5
SP  - 1442
VL  - 51
DO  - 10.1002/jhet.1752
UR  - conv_1130
ER  - 

@article{
author = "Rančić, Milica and Trisović, Nemanja and Milcić, Miloš and Jovanović, Maja and Jovanović, Bratislav and Marinković, Aleksandar",
year = "2014",
abstract = "Two series of 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines have been synthesized using different methods of conventional and microwave-assisted synthesis, and linear free-energy relationships have been applied to the C-13 NMR chemical shifts of the carbon atoms of interest. The substituent-induced chemical shifts have been analyzed using single substituent parameter and dual substituent parameter methods. The presented correlations describe satisfactorily the field and resonance substituent effects having similar contributions for C1 and the azomethine carbon, with exception of the carbon atom in para position to the substituent X. In both series, negative values have been found for C1 atom (reverse substituent effect). Quantum chemical calculations of the optimized geometries at MP2/6-31G++(d,p) level, together with C-13 NMR chemical shifts, give a better insight into the influence of the molecular conformation on the transmission of electronic substituent effects. The comparison of correlation results for different series of imines with phenyl, 4-nitrophenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl group attached at the azomethine carbon with the results for 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines for the same substituent set (X) indicates that a combination of the influences of electronic effects of the substituent X and the (1)-unit can be described as a sensitive balance of different resonance structures.",
journal = "Journal of Heterocyclic Chemistry",
title = "Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines",
pages = "1451-1442",
number = "5",
volume = "51",
doi = "10.1002/jhet.1752",
url = "conv_1130"
}

Rančić, M., Trisović, N., Milcić, M., Jovanović, M., Jovanović, B.,& Marinković, A.. (2014). Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines. in Journal of Heterocyclic Chemistry, 51(5), 1442-1451.
https://doi.org/10.1002/jhet.1752
conv_1130

Rančić M, Trisović N, Milcić M, Jovanović M, Jovanović B, Marinković A. Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines. in Journal of Heterocyclic Chemistry. 2014;51(5):1442-1451.
doi:10.1002/jhet.1752
conv_1130 .

Rančić, Milica, Trisović, Nemanja, Milcić, Miloš, Jovanović, Maja, Jovanović, Bratislav, Marinković, Aleksandar, "Linear Free-Energy Relationships Applied to the 13 C NMR Chemical Shifts in 4-Substituted N -[1-(Pyridine-3-and-4-yl)ethylidene]anilines" in Journal of Heterocyclic Chemistry, 51, no. 5 (2014):1442-1451,
https://doi.org/10.1002/jhet.1752 .,
conv_1130 .

TY  - JOUR
AU  - Đaković-Sekulić, Tatjana
AU  - Lozanov-Crvenković, Zagorka
AU  - Rančić, Milica
AU  - Trisović, Nemanja
AU  - Ušćumlić, Gordana
PY  - 2014
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/585
AB  - Quantitative structure-retention relationship (QSRR) study of retention data of thirteen 5-arylidene-2,4-thiazolidinediones obtained by reversed phase HPTLC. The effect of substituents attached to aryliden ring on the properties of TZD molecule, whose retention is closely correlated to the inhibitory activity, was investigated. PCA was used to show similarities/dissimilarities among the compounds. Stepwise regression models were calculated for each mobile phase modifier used. The obtained models were characterized by good fit and predictive abilities. The descriptors included in the models are connected with both lipophilic and donor/acceptor interactions.
T2  - Journal of Liquid Chromatography & Related Technologies
T1  - Substituent effects on chromatographic retention data of 5-arylidene-2,4-thiazolidinediones in qsar methodology
EP  - 2035
IS  - 14
SP  - 2021
VL  - 37
DO  - 10.1080/10826076.2013.825858
UR  - conv_1112
ER  - 

@article{
author = "Đaković-Sekulić, Tatjana and Lozanov-Crvenković, Zagorka and Rančić, Milica and Trisović, Nemanja and Ušćumlić, Gordana",
year = "2014",
abstract = "Quantitative structure-retention relationship (QSRR) study of retention data of thirteen 5-arylidene-2,4-thiazolidinediones obtained by reversed phase HPTLC. The effect of substituents attached to aryliden ring on the properties of TZD molecule, whose retention is closely correlated to the inhibitory activity, was investigated. PCA was used to show similarities/dissimilarities among the compounds. Stepwise regression models were calculated for each mobile phase modifier used. The obtained models were characterized by good fit and predictive abilities. The descriptors included in the models are connected with both lipophilic and donor/acceptor interactions.",
journal = "Journal of Liquid Chromatography & Related Technologies",
title = "Substituent effects on chromatographic retention data of 5-arylidene-2,4-thiazolidinediones in qsar methodology",
pages = "2035-2021",
number = "14",
volume = "37",
doi = "10.1080/10826076.2013.825858",
url = "conv_1112"
}

Đaković-Sekulić, T., Lozanov-Crvenković, Z., Rančić, M., Trisović, N.,& Ušćumlić, G.. (2014). Substituent effects on chromatographic retention data of 5-arylidene-2,4-thiazolidinediones in qsar methodology. in Journal of Liquid Chromatography & Related Technologies, 37(14), 2021-2035.
https://doi.org/10.1080/10826076.2013.825858
conv_1112

Đaković-Sekulić T, Lozanov-Crvenković Z, Rančić M, Trisović N, Ušćumlić G. Substituent effects on chromatographic retention data of 5-arylidene-2,4-thiazolidinediones in qsar methodology. in Journal of Liquid Chromatography & Related Technologies. 2014;37(14):2021-2035.
doi:10.1080/10826076.2013.825858
conv_1112 .

Đaković-Sekulić, Tatjana, Lozanov-Crvenković, Zagorka, Rančić, Milica, Trisović, Nemanja, Ušćumlić, Gordana, "Substituent effects on chromatographic retention data of 5-arylidene-2,4-thiazolidinediones in qsar methodology" in Journal of Liquid Chromatography & Related Technologies, 37, no. 14 (2014):2021-2035,
https://doi.org/10.1080/10826076.2013.825858 .,
conv_1112 .

TY  - JOUR
AU  - Rančić, Milica
AU  - Trisović, Nemanja
AU  - Milcić, Miloš K.
AU  - Ajaj, Ismail
AU  - Marinković, Aleksandar D.
PY  - 2013
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/499
AB  - The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidinediones have been performed by the use of quantum chemical methods. The calculated C-13 NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their C-13 NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with sigma using SSP (single substituent parameter), field (sigma(F)) and resonance (sigma(R)) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at C-beta. and C-7 carbons, while reverse substituent effect was found for C-alpha. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at C-alpha carbon causes increased sensitivity of SCS C-beta to the resonance effect with increasing of electron-accepting capabilities of the group present at C-beta.
T2  - Journal of Molecular Structure
T1  - Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones
EP  - 68
SP  - 59
VL  - 1049
DO  - 10.1016/j.molstruc.2013.06.027
UR  - conv_919
ER  - 

@article{
author = "Rančić, Milica and Trisović, Nemanja and Milcić, Miloš K. and Ajaj, Ismail and Marinković, Aleksandar D.",
year = "2013",
abstract = "The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidinediones have been performed by the use of quantum chemical methods. The calculated C-13 NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their C-13 NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with sigma using SSP (single substituent parameter), field (sigma(F)) and resonance (sigma(R)) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at C-beta. and C-7 carbons, while reverse substituent effect was found for C-alpha. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at C-alpha carbon causes increased sensitivity of SCS C-beta to the resonance effect with increasing of electron-accepting capabilities of the group present at C-beta.",
journal = "Journal of Molecular Structure",
title = "Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones",
pages = "68-59",
volume = "1049",
doi = "10.1016/j.molstruc.2013.06.027",
url = "conv_919"
}

Rančić, M., Trisović, N., Milcić, M. K., Ajaj, I.,& Marinković, A. D.. (2013). Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones. in Journal of Molecular Structure, 1049, 59-68.
https://doi.org/10.1016/j.molstruc.2013.06.027
conv_919

Rančić M, Trisović N, Milcić MK, Ajaj I, Marinković AD. Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones. in Journal of Molecular Structure. 2013;1049:59-68.
doi:10.1016/j.molstruc.2013.06.027
conv_919 .

Rančić, Milica, Trisović, Nemanja, Milcić, Miloš K., Ajaj, Ismail, Marinković, Aleksandar D., "Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones" in Journal of Molecular Structure, 1049 (2013):59-68,
https://doi.org/10.1016/j.molstruc.2013.06.027 .,
conv_919 .

TY  - JOUR
AU  - Rančić, Milica
AU  - Trisović, Nemanja
AU  - Milcić, Miloš
AU  - Ušćumlić, Gordana
AU  - Marinković, Aleksandar
PY  - 2012
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/462
AB  - The absorption spectra of twelve 5-arylidene-2,4-thiazolidinediones were recorded in twenty one solvents in the range from 300 to 600 nm. The effect of specific and non-specific solvent-solute interactions on the absorption maxima shifts were evaluated by using the Catalan solvent parameter set. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2 and time-dependent density functional (TD-DFT) methods. It was found that different substituents significantly change the extent of conjugation in the molecules and further affect their intramolecular charge transfer character.
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Substituent and solvent effects on intramolecular charge transfer of 5-arylidene-2,4-thiazolidinediones
EP  - 507
SP  - 500
VL  - 86
DO  - 10.1016/j.saa.2011.10.074
UR  - conv_1003
ER  - 

@article{
author = "Rančić, Milica and Trisović, Nemanja and Milcić, Miloš and Ušćumlić, Gordana and Marinković, Aleksandar",
year = "2012",
abstract = "The absorption spectra of twelve 5-arylidene-2,4-thiazolidinediones were recorded in twenty one solvents in the range from 300 to 600 nm. The effect of specific and non-specific solvent-solute interactions on the absorption maxima shifts were evaluated by using the Catalan solvent parameter set. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2 and time-dependent density functional (TD-DFT) methods. It was found that different substituents significantly change the extent of conjugation in the molecules and further affect their intramolecular charge transfer character.",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Substituent and solvent effects on intramolecular charge transfer of 5-arylidene-2,4-thiazolidinediones",
pages = "507-500",
volume = "86",
doi = "10.1016/j.saa.2011.10.074",
url = "conv_1003"
}

Rančić, M., Trisović, N., Milcić, M., Ušćumlić, G.,& Marinković, A.. (2012). Substituent and solvent effects on intramolecular charge transfer of 5-arylidene-2,4-thiazolidinediones. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 86, 500-507.
https://doi.org/10.1016/j.saa.2011.10.074
conv_1003

Rančić M, Trisović N, Milcić M, Ušćumlić G, Marinković A. Substituent and solvent effects on intramolecular charge transfer of 5-arylidene-2,4-thiazolidinediones. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2012;86:500-507.
doi:10.1016/j.saa.2011.10.074
conv_1003 .

Rančić, Milica, Trisović, Nemanja, Milcić, Miloš, Ušćumlić, Gordana, Marinković, Aleksandar, "Substituent and solvent effects on intramolecular charge transfer of 5-arylidene-2,4-thiazolidinediones" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 86 (2012):500-507,
https://doi.org/10.1016/j.saa.2011.10.074 .,
conv_1003 .