TY  - JOUR
AU  - Marković, Violeta
AU  - Marković, Svetlana
AU  - Janićijević, Ana
AU  - Rodić, Marko
AU  - Leovac, Vukadin M.
AU  - Todorović, Nina
AU  - Trifunović, Snežana S.
AU  - Joksović, Milan D.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1455
AB  - A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
VL  - 24
IS  - 6
SP  - 2127
EP  - 2136
DO  - 10.1007/s11224-013-0223-3
ER  - 

@article{
author = "Marković, Violeta and Marković, Svetlana and Janićijević, Ana and Rodić, Marko and Leovac, Vukadin M. and Todorović, Nina and Trifunović, Snežana S. and Joksović, Milan D.",
year = "2013",
abstract = "A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate",
volume = "24",
number = "6",
pages = "2127-2136",
doi = "10.1007/s11224-013-0223-3"
}

Marković, V., Marković, S., Janićijević, A., Rodić, M., Leovac, V. M., Todorović, N., Trifunović, S. S.,& Joksović, M. D.. (2013). Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry
Springer/Plenum Publishers, New York., 24(6), 2127-2136.
https://doi.org/10.1007/s11224-013-0223-3

Marković V, Marković S, Janićijević A, Rodić M, Leovac VM, Todorović N, Trifunović SS, Joksović MD. Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry. 2013;24(6):2127-2136.
doi:10.1007/s11224-013-0223-3 .

Marković, Violeta, Marković, Svetlana, Janićijević, Ana, Rodić, Marko, Leovac, Vukadin M., Todorović, Nina, Trifunović, Snežana S., Joksović, Milan D., "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate" in Structural Chemistry, 24, no. 6 (2013):2127-2136,
https://doi.org/10.1007/s11224-013-0223-3 . .

TY  - DATA
AU  - Marković, Violeta
AU  - Janićijević, Ana
AU  - Stanojković, Tatjana
AU  - Kolundžija, Branka
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksović, Ljubinka
AU  - Đurđević, Predrag T.
AU  - Todorović, Nina
AU  - Trifunović, Snežana S.
AU  - Joksović, Milan D.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3548
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3548
ER  - 

@misc{
author = "Marković, Violeta and Janićijević, Ana and Stanojković, Tatjana and Kolundžija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksović, Ljubinka and Đurđević, Predrag T. and Todorović, Nina and Trifunović, Snežana S. and Joksović, Milan D.",
year = "2013",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3548"
}

Marković, V., Janićijević, A., Stanojković, T., Kolundžija, B., Sladić, D., Vujčić, M., Janović, B., Joksović, L., Đurđević, P. T., Todorović, N., Trifunović, S. S.,& Joksović, M. D.. (2013). Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris..
https://hdl.handle.net/21.15107/rcub_cherry_3548

Marković V, Janićijević A, Stanojković T, Kolundžija B, Sladić D, Vujčić M, Janović B, Joksović L, Đurđević PT, Todorović N, Trifunović SS, Joksović MD. Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071. in European Journal of Medicinal Chemistry. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3548 .

Marković, Violeta, Janićijević, Ana, Stanojković, Tatjana, Kolundžija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksović, Ljubinka, Đurđević, Predrag T., Todorović, Nina, Trifunović, Snežana S., Joksović, Milan D., "Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071" in European Journal of Medicinal Chemistry (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3548 .

TY  - JOUR
AU  - Marković, Violeta
AU  - Janićijević, Ana
AU  - Stanojković, Tatjana
AU  - Kolundžija, Branka
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksović, Ljubinka
AU  - Đurđević, Predrag T.
AU  - Todorović, Nina
AU  - Trifunović, Snežana S.
AU  - Joksović, Milan D.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1370
AB  - A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group
VL  - 64
SP  - 228
EP  - 238
DO  - 10.1016/j.ejmech.2013.03.071
ER  - 

@article{
author = "Marković, Violeta and Janićijević, Ana and Stanojković, Tatjana and Kolundžija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksović, Ljubinka and Đurđević, Predrag T. and Todorović, Nina and Trifunović, Snežana S. and Joksović, Milan D.",
year = "2013",
abstract = "A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group",
volume = "64",
pages = "228-238",
doi = "10.1016/j.ejmech.2013.03.071"
}

Marković, V., Janićijević, A., Stanojković, T., Kolundžija, B., Sladić, D., Vujčić, M., Janović, B., Joksović, L., Đurđević, P. T., Todorović, N., Trifunović, S. S.,& Joksović, M. D.. (2013). Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 64, 228-238.
https://doi.org/10.1016/j.ejmech.2013.03.071

Marković V, Janićijević A, Stanojković T, Kolundžija B, Sladić D, Vujčić M, Janović B, Joksović L, Đurđević PT, Todorović N, Trifunović SS, Joksović MD. Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry. 2013;64:228-238.
doi:10.1016/j.ejmech.2013.03.071 .

Marković, Violeta, Janićijević, Ana, Stanojković, Tatjana, Kolundžija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksović, Ljubinka, Đurđević, Predrag T., Todorović, Nina, Trifunović, Snežana S., Joksović, Milan D., "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group" in European Journal of Medicinal Chemistry, 64 (2013):228-238,
https://doi.org/10.1016/j.ejmech.2013.03.071 . .