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Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone

Glamočlija, Una; Padhye, Subhash; Špirtović- Halilović, Selma; Osmanović, Amar; Veljović, Elma; Roca, Sunčica; Novaković, Irena; Mandić, Boris; Turel, Iztok; Kljun, Jakob; Trifunović, Snežana; Kahrović, Emira; Kraljević Pavelić, Sandra; Harej, Anja; Klobučar, Marko; Završnik, Davorka (2018) Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone. Molecules, 23 (12). pp. 3297-3313. ISSN 1420-3049

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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. Themost potentwas 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.

Item Type: Article
Uncontrolled Keywords: thymoquinone ; benzoxazoles ; anticancer activity ; antimicrobial activity ; western blotting ; molecular docking
Subjects: NATURAL SCIENCES > Chemistry
Divisions: NMR Center
Depositing User: Sunčica Roca
Date Deposited: 12 Feb 2019 08:53
Last Modified: 12 Feb 2019 08:55
URI: http://fulir.irb.hr/id/eprint/4415
DOI: 10.3390/molecules23123297

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