20.500.12556/RUL-131999 Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone 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 ($^1$H, $^{13}$C) 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. thymoquinone benzoxazoles anticancer activity antimicrobial activity western blotting molecular docking benzoksazoli timokinon protimikrobno delovanje protirakavo delovanje true false true Angleški jezik Slovenski jezik Članek v reviji 2021-10-08 09:53:10 2021-10-08 09:53:11 2022-09-12 04:10:35 0000-00-00 00:00:00 2018 0 0 17 str. iss. 12, art. 3297 Vol. 23 2018 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.78.057 1420-3049 10.3390/molecules23123297 1538073795 RAZ_Glamoclija_Una_2018.pdf RAZ_Glamoclija_Una_2018.pdf 1 EE633F7410234DFB14DCBA47A5A313D4 217fa9f6d7efc97d62837d0da66568e6e0bd2579706fb40cd513a86e0c5970a3 3b6e93ad-280d-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=149484 https://www.mdpi.com/1420-3049/23/12/3297 0 7d063350-280c-11ec-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=149482 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0