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: Una Glamo člija Subhash Padhye Selma Špirtović-Halilović Amar Osmanovi ć Elma Veljovi ć Sun čica Roca Irena Novakovi ć Boris Mandi ć Iztok Turel Jakob Kljun Sne žana Trifunović Emira Kahrovi ć Sandra Kraljevi ć Pavelić Anja Harej Marko Klobu Tags: Article Source Type: research