TY  - JOUR
AU  - Spirtović-Halilović, Selma
AU  - Salihović, Mirsada
AU  - Osmanović, Amar
AU  - Veljović, Elma
AU  - Rahić, O.
AU  - Mahmutović, E.
AU  - Hadziabdi, J.
AU  - Novaković, Irena
AU  - Roca, S.
AU  - Trifunović, Snežana
AU  - Elezović, Alisa
AU  - Glamoclija, Una
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7043
AB  - In the reaction of 3-aminothymoquinone and aromatic aldehydes, two benzoxazole derivatives viz. 2-(4-methoxyphenyl)-4-methyl-7-isopropyl-1,3-benzoxazol-5-ol (1) and 2-(4-trifluoromethyl)-4-methyl-7-isopropyl-1,3-benzoxazol-5-ol (2) were prepared and characterized by elemental analysis, infrared and 1H, and 13C-nuclear magnetic resonance spectroscopy and mass spectrometry. Their antimicrobial activity against Escherichia coli, Salmonella enterica, Proteus hauseri, Pseudomonas aeruginosa, Staphylococcus aureus, Sarcina lutea, Clostridium sporogenes and Bacillus subtilis was tested. Synthesized compounds show the best activity on Sarcina lutea, and the lowest against Proteus hauseri and Clostridium sporogenes. The paper assesses in silico methods of the possible ways selected derivatives bind to the enzyme deoxyribonucleic acid gyrase (1KZN). The docking results were compared with those obtained from in vitro antimicrobial activity. Molecular properties and absorption, distribution, metabolism and excretion parameters were also calculated for compounds. The difference in the obtained values reflects differences in the derivatives structures. In the future, tests on a number of enzymes crucial for bacterial life as well as a number of derivatives may offer further information on the mechanisms of action of these substances.
PB  - Indian Pharmaceutical Association - IPA
T2  - Indian Journal of Pharmaceutical Sciences
T1  - In Silico Study of Microbiologically Active Benzoxazole Derivatives
VL  - 85
IS  - 3
SP  - 767
EP  - 777
DO  - 10.36468/pharmaceutical-sciences.1143
ER  - 

@article{
author = "Spirtović-Halilović, Selma and Salihović, Mirsada and Osmanović, Amar and Veljović, Elma and Rahić, O. and Mahmutović, E. and Hadziabdi, J. and Novaković, Irena and Roca, S. and Trifunović, Snežana and Elezović, Alisa and Glamoclija, Una",
year = "2023",
abstract = "In the reaction of 3-aminothymoquinone and aromatic aldehydes, two benzoxazole derivatives viz. 2-(4-methoxyphenyl)-4-methyl-7-isopropyl-1,3-benzoxazol-5-ol (1) and 2-(4-trifluoromethyl)-4-methyl-7-isopropyl-1,3-benzoxazol-5-ol (2) were prepared and characterized by elemental analysis, infrared and 1H, and 13C-nuclear magnetic resonance spectroscopy and mass spectrometry. Their antimicrobial activity against Escherichia coli, Salmonella enterica, Proteus hauseri, Pseudomonas aeruginosa, Staphylococcus aureus, Sarcina lutea, Clostridium sporogenes and Bacillus subtilis was tested. Synthesized compounds show the best activity on Sarcina lutea, and the lowest against Proteus hauseri and Clostridium sporogenes. The paper assesses in silico methods of the possible ways selected derivatives bind to the enzyme deoxyribonucleic acid gyrase (1KZN). The docking results were compared with those obtained from in vitro antimicrobial activity. Molecular properties and absorption, distribution, metabolism and excretion parameters were also calculated for compounds. The difference in the obtained values reflects differences in the derivatives structures. In the future, tests on a number of enzymes crucial for bacterial life as well as a number of derivatives may offer further information on the mechanisms of action of these substances.",
publisher = "Indian Pharmaceutical Association - IPA",
journal = "Indian Journal of Pharmaceutical Sciences",
title = "In Silico Study of Microbiologically Active Benzoxazole Derivatives",
volume = "85",
number = "3",
pages = "767-777",
doi = "10.36468/pharmaceutical-sciences.1143"
}

Spirtović-Halilović, S., Salihović, M., Osmanović, A., Veljović, E., Rahić, O., Mahmutović, E., Hadziabdi, J., Novaković, I., Roca, S., Trifunović, S., Elezović, A.,& Glamoclija, U.. (2023). In Silico Study of Microbiologically Active Benzoxazole Derivatives. in Indian Journal of Pharmaceutical Sciences
Indian Pharmaceutical Association - IPA., 85(3), 767-777.
https://doi.org/10.36468/pharmaceutical-sciences.1143

Spirtović-Halilović S, Salihović M, Osmanović A, Veljović E, Rahić O, Mahmutović E, Hadziabdi J, Novaković I, Roca S, Trifunović S, Elezović A, Glamoclija U. In Silico Study of Microbiologically Active Benzoxazole Derivatives. in Indian Journal of Pharmaceutical Sciences. 2023;85(3):767-777.
doi:10.36468/pharmaceutical-sciences.1143 .

Spirtović-Halilović, Selma, Salihović, Mirsada, Osmanović, Amar, Veljović, Elma, Rahić, O., Mahmutović, E., Hadziabdi, J., Novaković, Irena, Roca, S., Trifunović, Snežana, Elezović, Alisa, Glamoclija, Una, "In Silico Study of Microbiologically Active Benzoxazole Derivatives" in Indian Journal of Pharmaceutical Sciences, 85, no. 3 (2023):767-777,
https://doi.org/10.36468/pharmaceutical-sciences.1143 . .

TY  - JOUR
AU  - Glamoclija, Una
AU  - Padhye, Subhash
AU  - Spirtovic-Halilovic, Selma
AU  - Osmanovic, Amar
AU  - Veljović, Elma
AU  - Roca, Suncica
AU  - Novaković, Irena
AU  - Mandić, Boris
AU  - Turel, Iztok
AU  - Kljun, Jakob
AU  - Trifunović, Snežana
AU  - Kahrovic, Emira
AU  - Kraljević Pavelić, Sandra
AU  - Harej, Anja
AU  - Klobucar, Marko
AU  - Zavrsnik, Davorka
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2403
AB  - Thymoquinone (TQ), a natural compound with antimicrobial and antitumor activity, was used as the starting molecule for the preparation of 3-aminothymoquinone (ATQ) from which ten novel benzoxazole derivatives were prepared and characterized by elemental analysis, IR spectroscopy, mass spectrometry and NMR (H-1, C-13) spectroscopy in solution. The crystal structure of 4-methyl-2-phenyl-7-isopropyl-1,3-benzoxazole-5-ol (1a) has been determined by X-ray diffraction. All compounds were tested for their antibacterial, antifungal and antitumor activities. TQ and ATQ showed better antibacterial activity against tested Gram-positive and Gram-negative bacterial strains than benzoxazoles. ATQ had the most potent antifungal effect against Candida albicans, Saccharomyces cerevisiae and Aspergillus brasiliensis. Three benzoxazole derivatives and ATQ showed the highest antitumor activities. The most potent was 2-(4-fluorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1f). Western blot analyses have shown that this compound inhibited phosphorylation of protein kinase B (Akt) and Insulin-like Growth Factor-1 Receptor (IGF1R ) in HeLa and HepG2 cells. The least toxic compound against normal fibroblast cells, which maintains similar antitumor activities as TQ, was 2-(4-chlorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1e). Docking studies indicated that 1e and 1f have significant effects against selected receptors playing important roles in tumour survival.
PB  - MDPI
T2  - Molecules
T1  - Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone
VL  - 23
IS  - 12
DO  - 10.3390/molecules23123297
ER  - 

@article{
author = "Glamoclija, Una and Padhye, Subhash and Spirtovic-Halilovic, Selma and Osmanovic, Amar and Veljović, Elma and Roca, Suncica and Novaković, Irena and Mandić, Boris and Turel, Iztok and Kljun, Jakob and Trifunović, Snežana and Kahrovic, Emira and Kraljević Pavelić, Sandra and Harej, Anja and Klobucar, Marko and Zavrsnik, Davorka",
year = "2018",
abstract = "Thymoquinone (TQ), a natural compound with antimicrobial and antitumor activity, was used as the starting molecule for the preparation of 3-aminothymoquinone (ATQ) from which ten novel benzoxazole derivatives were prepared and characterized by elemental analysis, IR spectroscopy, mass spectrometry and NMR (H-1, C-13) spectroscopy in solution. The crystal structure of 4-methyl-2-phenyl-7-isopropyl-1,3-benzoxazole-5-ol (1a) has been determined by X-ray diffraction. All compounds were tested for their antibacterial, antifungal and antitumor activities. TQ and ATQ showed better antibacterial activity against tested Gram-positive and Gram-negative bacterial strains than benzoxazoles. ATQ had the most potent antifungal effect against Candida albicans, Saccharomyces cerevisiae and Aspergillus brasiliensis. Three benzoxazole derivatives and ATQ showed the highest antitumor activities. The most potent was 2-(4-fluorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1f). Western blot analyses have shown that this compound inhibited phosphorylation of protein kinase B (Akt) and Insulin-like Growth Factor-1 Receptor (IGF1R ) in HeLa and HepG2 cells. The least toxic compound against normal fibroblast cells, which maintains similar antitumor activities as TQ, was 2-(4-chlorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1e). Docking studies indicated that 1e and 1f have significant effects against selected receptors playing important roles in tumour survival.",
publisher = "MDPI",
journal = "Molecules",
title = "Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone",
volume = "23",
number = "12",
doi = "10.3390/molecules23123297"
}

Glamoclija, U., Padhye, S., Spirtovic-Halilovic, S., Osmanovic, A., Veljović, E., Roca, S., Novaković, I., Mandić, B., Turel, I., Kljun, J., Trifunović, S., Kahrovic, E., Kraljević Pavelić, S., Harej, A., Klobucar, M.,& Zavrsnik, D.. (2018). Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone. in Molecules
MDPI., 23(12).
https://doi.org/10.3390/molecules23123297

Glamoclija U, Padhye S, Spirtovic-Halilovic S, Osmanovic A, Veljović E, Roca S, Novaković I, Mandić B, Turel I, Kljun J, Trifunović S, Kahrovic E, Kraljević Pavelić S, Harej A, Klobucar M, Zavrsnik D. Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone. in Molecules. 2018;23(12).
doi:10.3390/molecules23123297 .

Glamoclija, Una, Padhye, Subhash, Spirtovic-Halilovic, Selma, Osmanovic, Amar, Veljović, Elma, Roca, Suncica, Novaković, Irena, Mandić, Boris, Turel, Iztok, Kljun, Jakob, Trifunović, Snežana, Kahrovic, Emira, Kraljević Pavelić, Sandra, Harej, Anja, Klobucar, Marko, Zavrsnik, Davorka, "Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone" in Molecules, 23, no. 12 (2018),
https://doi.org/10.3390/molecules23123297 . .