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

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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)
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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
Funding / 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 ]
10
10
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2403
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Glamoclija, Una
AU  - Padhye, Subhash
AU  - Spirtovic-Halilovic, Selma
AU  - Osmanovic, Amar
AU  - Veljović, Elma
AU  - Roca, Suncica
AU  - Novaković, Irena
AU  - Mandić, Boris
AU  - Turel, Iztok
AU  - Kljun, Jakob
AU  - Trifunović, Snežana
AU  - Kahrovic, Emira
AU  - Kraljević Pavelić, Sandra
AU  - Harej, Anja
AU  - Klobucar, Marko
AU  - Zavrsnik, Davorka
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2403
AB  - 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 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.
PB  - MDPI
T2  - Molecules
T1  - Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone
VL  - 23
IS  - 12
DO  - 10.3390/molecules23123297
ER  - 
@article{
author = "Glamoclija, Una and Padhye, Subhash and Spirtovic-Halilovic, Selma and Osmanovic, Amar and Veljović, Elma and Roca, Suncica and Novaković, Irena and Mandić, Boris and Turel, Iztok and Kljun, Jakob and Trifunović, Snežana and Kahrovic, Emira and Kraljević Pavelić, Sandra and Harej, Anja and Klobucar, Marko and Zavrsnik, Davorka",
year = "2018",
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 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.",
publisher = "MDPI",
journal = "Molecules",
title = "Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone",
volume = "23",
number = "12",
doi = "10.3390/molecules23123297"
}
Glamoclija, U., Padhye, S., Spirtovic-Halilovic, S., Osmanovic, A., Veljović, E., Roca, S., Novaković, I., Mandić, B., Turel, I., Kljun, J., Trifunović, S., Kahrovic, E., Kraljević Pavelić, S., Harej, A., Klobucar, M.,& Zavrsnik, D.. (2018). Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone. in Molecules
MDPI., 23(12).
https://doi.org/10.3390/molecules23123297
Glamoclija U, Padhye S, Spirtovic-Halilovic S, Osmanovic A, Veljović E, Roca S, Novaković I, Mandić B, Turel I, Kljun J, Trifunović S, Kahrovic E, Kraljević Pavelić S, Harej A, Klobucar M, Zavrsnik D. Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone. in Molecules. 2018;23(12).
doi:10.3390/molecules23123297 .
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, "Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone" in Molecules, 23, no. 12 (2018),
https://doi.org/10.3390/molecules23123297 . .

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