TY  - JOUR
AU  - Božić, Aleksandra R.
AU  - Filipović, Nenad
AU  - Verbić, Tatjana Z.
AU  - Milcić, Milos K.
AU  - Todorović, Tamara R.
AU  - Cvijetić, Ilija N.
AU  - Klisurić, Olivera
AU  - Radisić, Marina M.
AU  - Marinković, Aleksandar D.
PY  - 2020
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/5363
AB  - The substituent and solvent effect on intramolecular charge transfer (ICT) of twelve monocarbohydrazones (mCHs) were studied using experimental and theoretical methodology. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear free energy relationships (LFERs) principles, i.e. using the Kamlet-Taft and Catalan models. Linear free energy relationships in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on UV-Vis, NMR and pK(a) change. According to crystallographic data and quantum chemical calculations, the trans (E) form was found to be more stable. A photochromism of compounds with 2-hydroxyphenyl and 2-pyridylimino groups substituted at imine carbon atom results in E/Z isomerization due to creation of intermolecular hydrogen bond in E and Z form, respectively. Multiple stage mass spectrometry (MS-MSn) analysis was applied to define main fragmentation pathways. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2/6-311 G(d,p) and time-dependent density functional (TD-DFT) methods. TD-DFT calculations were performed to quantify the efficiency of intramolecular charge transfer (ICT) with the aid of the charge-transfer distance (DCT) and the amount of transferred charge (QCT) calculation. It was found that both substituents and solvents influence electron density shift i.e. extent of conjugation, and affect ICT character in the course of excitation.
PB  - Elsevier, Amsterdam
T2  - Arabian Journal of Chemistry
T1  - A detailed experimental and computational study of monocarbohydrazones
EP  - 953
IS  - 1
SP  - 932
VL  - 13
DO  - 10.1016/j.arabjc.2017.08.010
ER  - 

@article{
author = "Božić, Aleksandra R. and Filipović, Nenad and Verbić, Tatjana Z. and Milcić, Milos K. and Todorović, Tamara R. and Cvijetić, Ilija N. and Klisurić, Olivera and Radisić, Marina M. and Marinković, Aleksandar D.",
year = "2020",
abstract = "The substituent and solvent effect on intramolecular charge transfer (ICT) of twelve monocarbohydrazones (mCHs) were studied using experimental and theoretical methodology. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear free energy relationships (LFERs) principles, i.e. using the Kamlet-Taft and Catalan models. Linear free energy relationships in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on UV-Vis, NMR and pK(a) change. According to crystallographic data and quantum chemical calculations, the trans (E) form was found to be more stable. A photochromism of compounds with 2-hydroxyphenyl and 2-pyridylimino groups substituted at imine carbon atom results in E/Z isomerization due to creation of intermolecular hydrogen bond in E and Z form, respectively. Multiple stage mass spectrometry (MS-MSn) analysis was applied to define main fragmentation pathways. Furthermore, the experimental findings were interpreted with the aid of ab initio MP2/6-311 G(d,p) and time-dependent density functional (TD-DFT) methods. TD-DFT calculations were performed to quantify the efficiency of intramolecular charge transfer (ICT) with the aid of the charge-transfer distance (DCT) and the amount of transferred charge (QCT) calculation. It was found that both substituents and solvents influence electron density shift i.e. extent of conjugation, and affect ICT character in the course of excitation.",
publisher = "Elsevier, Amsterdam",
journal = "Arabian Journal of Chemistry",
title = "A detailed experimental and computational study of monocarbohydrazones",
pages = "953-932",
number = "1",
volume = "13",
doi = "10.1016/j.arabjc.2017.08.010"
}

Božić, A. R., Filipović, N., Verbić, T. Z., Milcić, M. K., Todorović, T. R., Cvijetić, I. N., Klisurić, O., Radisić, M. M.,& Marinković, A. D.. (2020). A detailed experimental and computational study of monocarbohydrazones. in Arabian Journal of Chemistry
Elsevier, Amsterdam., 13(1), 932-953.
https://doi.org/10.1016/j.arabjc.2017.08.010

Božić AR, Filipović N, Verbić TZ, Milcić MK, Todorović TR, Cvijetić IN, Klisurić O, Radisić MM, Marinković AD. A detailed experimental and computational study of monocarbohydrazones. in Arabian Journal of Chemistry. 2020;13(1):932-953.
doi:10.1016/j.arabjc.2017.08.010 .

Božić, Aleksandra R., Filipović, Nenad, Verbić, Tatjana Z., Milcić, Milos K., Todorović, Tamara R., Cvijetić, Ilija N., Klisurić, Olivera, Radisić, Marina M., Marinković, Aleksandar D., "A detailed experimental and computational study of monocarbohydrazones" in Arabian Journal of Chemistry, 13, no. 1 (2020):932-953,
https://doi.org/10.1016/j.arabjc.2017.08.010 . .

TY  - JOUR
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana
AU  - Novaković, Irena
AU  - Filipović, Nenad
AU  - Petrović, Predrag M.
AU  - Marinković, Aleksandar D.
AU  - Todorović, Tamara R.
AU  - Cvijetić, Ilija N.
PY  - 2018
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/4753
AB  - Due to the rise of microbial strains resistant to conventional therapies, there is an urgent need for finding the new antimicrobial chemotypes. Heterocyclic compounds such as thiocarbohydrazones (TCHs) are able to interact with many metalloenzymes essential for microbes, while sulfur atom increases lipophilicity which is generally positively correlated with potency. In this paper, we report antibacterial and antifungal activity of twenty-two TCHs toward eight bacterial and three fungal strains. Furthermore, three alignment independent 3D QSAR models based on descriptors derived from molecular interaction fields (MIFs) are developed in order to rationalize structure-activity relationships for activities of TCHs toward S. aureus, P. aeruginosa and C. albicans. Several structural fragments important for biological activity are recognized in each model, and structural modifications which could lead to increased potency are suggested. Designed structures will be synthesized accordingly and tested toward the same microbial strains in order to obtain more potent derivatives.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemistryselect
T1  - Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models
EP  - 2221
IS  - 7
SP  - 2215
VL  - 3
DO  - 10.1002/slct.201702691
ER  - 

@article{
author = "Božić, Aleksandra R. and Bjelogrlić, Snežana and Novaković, Irena and Filipović, Nenad and Petrović, Predrag M. and Marinković, Aleksandar D. and Todorović, Tamara R. and Cvijetić, Ilija N.",
year = "2018",
abstract = "Due to the rise of microbial strains resistant to conventional therapies, there is an urgent need for finding the new antimicrobial chemotypes. Heterocyclic compounds such as thiocarbohydrazones (TCHs) are able to interact with many metalloenzymes essential for microbes, while sulfur atom increases lipophilicity which is generally positively correlated with potency. In this paper, we report antibacterial and antifungal activity of twenty-two TCHs toward eight bacterial and three fungal strains. Furthermore, three alignment independent 3D QSAR models based on descriptors derived from molecular interaction fields (MIFs) are developed in order to rationalize structure-activity relationships for activities of TCHs toward S. aureus, P. aeruginosa and C. albicans. Several structural fragments important for biological activity are recognized in each model, and structural modifications which could lead to increased potency are suggested. Designed structures will be synthesized accordingly and tested toward the same microbial strains in order to obtain more potent derivatives.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemistryselect",
title = "Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models",
pages = "2221-2215",
number = "7",
volume = "3",
doi = "10.1002/slct.201702691"
}

Božić, A. R., Bjelogrlić, S., Novaković, I., Filipović, N., Petrović, P. M., Marinković, A. D., Todorović, T. R.,& Cvijetić, I. N.. (2018). Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models. in Chemistryselect
Wiley-V C H Verlag Gmbh, Weinheim., 3(7), 2215-2221.
https://doi.org/10.1002/slct.201702691

Božić AR, Bjelogrlić S, Novaković I, Filipović N, Petrović PM, Marinković AD, Todorović TR, Cvijetić IN. Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models. in Chemistryselect. 2018;3(7):2215-2221.
doi:10.1002/slct.201702691 .

Božić, Aleksandra R., Bjelogrlić, Snežana, Novaković, Irena, Filipović, Nenad, Petrović, Predrag M., Marinković, Aleksandar D., Todorović, Tamara R., Cvijetić, Ilija N., "Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment-Independent 3D QSAR Models" in Chemistryselect, 3, no. 7 (2018):2215-2221,
https://doi.org/10.1002/slct.201702691 . .