CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrilic)
    • Serbian (Latin)
  • Login
View Item 
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

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

Thumbnail
2018
2401.pdf (2.915Mb)
Authors
Glamoclija, Una
Padhye, Subhash
Spirtovic-Halilovic, Selma
Osmanovic, Amar
Veljović, Elma
Roca, Suncica
Novaković, Irena
Mandić, Boris
Turel, Iztok
Kljun, Jakob
Trifunović, Snežana
Kahrovic, Emira
Kraljević Pavelić, Sandra
Harej, Anja
Klobucar, Marko
Zavrsnik, Davorka
Article (Published version)
Metadata
Show full item record
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 (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 h...ave 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.

Keywords:
thymoquinone / benzoxazoles / anticancer activity / antimicrobial activity / western blotting / molecular docking
Source:
Molecules, 2018, 23, 12
Publisher:
  • MDPI AG
Projects:
  • Federal Ministry of education and science in Bosnia and Herzegovina - 05-39-3629-1/14
  • Ministarstvo za obrazovanje, nauku, kulturu i sport FBiH, 2014-2015 - 05-39-3629-1/14

DOI: 10.3390/molecules23123297

ISSN: 1420-3049

PubMed: 30545123

WoS: 000454523000247

Scopus: 2-s2.0-85058766907
[ Google Scholar ]
4
5
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2403
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutionsAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB