Molecules, Vol. 23, Pages 3297: Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone

Molecules, Vol. 23, Pages 3297: Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone Molecules doi: 10.3390/molecules23123297 Authors: Una Glamočlija Subhash Padhye Selma Špirtović-Halilović Amar Osmanović Elma Veljović Sunčica Roca Irena Novaković Boris Mandić Iztok Turel Jakob Kljun Snežana Trifunović Emira Kahrović Sandra Kraljević Pavelić Anja Harej Marko Klobučar Davorka Završnik 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 thi...
Source: Molecules - Category: Chemistry Authors: Tags: Article Source Type: research