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dc.creatorGlamoclija, Una
dc.creatorPadhye, Subhash
dc.creatorSpirtovic-Halilovic, Selma
dc.creatorOsmanovic, Amar
dc.creatorVeljović, Elma
dc.creatorRoca, Suncica
dc.creatorNovaković, Irena
dc.creatorMandić, Boris
dc.creatorTurel, Iztok
dc.creatorKljun, Jakob
dc.creatorTrifunović, Snežana
dc.creatorKahrovic, Emira
dc.creatorKraljević Pavelić, Sandra
dc.creatorHarej, Anja
dc.creatorKlobucar, Marko
dc.creatorZavrsnik, Davorka
dc.date.accessioned2019-01-30T17:59:47Z
dc.date.available2019-01-30T17:59:47Z
dc.date.issued2018
dc.identifier.issn1420-3049
dc.identifier.urihttps://cer.ihtm.bg.ac.rs/handle/123456789/2403
dc.description.abstractThymoquinone (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 (H-1, C-13) 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 ) 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.en
dc.publisherMDPI
dc.relationFederal Ministry of education and science in Bosnia and Herzegovina - 05-39-3629-1/14
dc.relationMinistarstvo za obrazovanje, nauku, kulturu i sport FBiH, 2014-2015 - 05-39-3629-1/14
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.sourceMolecules
dc.subjectthymoquinoneen
dc.subjectbenzoxazolesen
dc.subjectanticancer activityen
dc.subjectantimicrobial activityen
dc.subjectwestern blottingen
dc.subjectmolecular dockingen
dc.titleSynthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinoneen
dc.typearticle
dc.rights.licenseBY
dcterms.abstractКахровиц, Емира; Кљун, Јакоб; Хареј, Aња; Клобуцар, Марко; Заврсник, Даворка; Гламоцлија, Уна; Павелиц, Сандра Краљевиц; Турел, Изток; Новаковић, Ирена; Падхyе, Субхасх; Трифуновиц, Снезана; Спиртовиц-Халиловиц, Селма; Османовиц, Aмар; Вељовиц, Елма; Роца, Сунцица; Мандиц, Борис;
dc.citation.volume23
dc.citation.issue12
dc.citation.other23(12):
dc.citation.rankM22
dc.identifier.pmid30545123
dc.identifier.doi10.3390/molecules23123297
dc.identifier.fulltexthttps://cer.ihtm.bg.ac.rs//bitstream/id/8772/2401.pdf
dc.identifier.scopus2-s2.0-85058766907
dc.identifier.wos000454523000247
dc.type.versionpublishedVersion


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