TY  - JOUR
AU  - Glamočlija, Una
AU  - Padhye, Subhash
AU  - Špirtović-Halilović, Selma
AU  - Osmanović, Amar
AU  - Veljović, Elma
AU  - Roca, Sunčica
AU  - Novaković, Irena T.
AU  - Mandić, Boris
AU  - Turel, Iztok
AU  - Kljun, Jakob
AU  - Trifunović, Snežana S.
AU  - Kahrović, Emira
AU  - Pavelić-Kraljević, Sandra
AU  - Harej, Anja
AU  - Klobučar, Marko
AU  - Završnik, Davorka
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2807
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 (1H,13C) 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 β) 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 = "Glamočlija, Una and Padhye, Subhash and Špirtović-Halilović, Selma and Osmanović, Amar and Veljović, Elma and Roca, Sunčica and Novaković, Irena T. and Mandić, Boris and Turel, Iztok and Kljun, Jakob and Trifunović, Snežana S. and Kahrović, Emira and Pavelić-Kraljević, Sandra and Harej, Anja and Klobučar, Marko and Završnik, 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 (1H,13C) 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 β) 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"
}

Glamočlija, U., Padhye, S., Špirtović-Halilović, S., Osmanović, A., Veljović, E., Roca, S., Novaković, I. T., Mandić, B., Turel, I., Kljun, J., Trifunović, S. S., Kahrović, E., Pavelić-Kraljević, S., Harej, A., Klobučar, M.,& Završnik, D.. (2018). Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone. in Molecules
MDPI., 23(12).
https://doi.org/10.3390/molecules23123297

Glamočlija U, Padhye S, Špirtović-Halilović S, Osmanović A, Veljović E, Roca S, Novaković IT, Mandić B, Turel I, Kljun J, Trifunović SS, Kahrović E, Pavelić-Kraljević S, Harej A, Klobučar M, Završnik D. Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone. in Molecules. 2018;23(12).
doi:10.3390/molecules23123297 .

Glamočlija, Una, Padhye, Subhash, Špirtović-Halilović, Selma, Osmanović, Amar, Veljović, Elma, Roca, Sunčica, Novaković, Irena T., Mandić, Boris, Turel, Iztok, Kljun, Jakob, Trifunović, Snežana S., Kahrović, Emira, Pavelić-Kraljević, Sandra, Harej, Anja, Klobučar, Marko, Završnik, Davorka, "Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone" in Molecules, 23, no. 12 (2018),
https://doi.org/10.3390/molecules23123297 . .