Modification of benzoxazole derivative by bromine-spectroscopic, antibacterial and reactivity study using experimental and theoretical procedures

N-[2-(2-bromophenyl)-1,3-benzoxazol-5-yl]-2-phenylacetamide (NBBPA) was synthesized in this study as an original compound in order to evaluate its antibacterial activity against representative Gram-negative and Gram-positive bacteria, with their drug-resistant clinical isolate. Microbiological resul...

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Bibliographic Details
Published in:Journal of molecular structure 2017-08, Vol.1141, p.495-511
Main Authors: Aswathy, V.V., Alper-Hayta, Sabiha, Yalcin, Gözde, Mary, Y. Sheena, Panicker, C. Yohannan, Jojo, P.J., Kaynak-Onurdag, Fatma, Armaković, Stevan, Armaković, Sanja J., Yildiz, Ilkay, Van Alsenoy, C.
Format: Article
Language:English
Subjects:
ALIE
Antibacterial activity
BDE
Benzoxazole
Moleculardocking
RDF
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Summary:N-[2-(2-bromophenyl)-1,3-benzoxazol-5-yl]-2-phenylacetamide (NBBPA) was synthesized in this study as an original compound in order to evaluate its antibacterial activity against representative Gram-negative and Gram-positive bacteria, with their drug-resistant clinical isolate. Microbiological results showed that this compound had moderate antibacterial activity. Study also encompassed detailed FT-IR, FT-Raman and NMR experimental and theoretical spectroscopic characterization and assignation of the ring breathing modes of the mono-, ortho- and tri-substituted phenyl rings is in agreement with the literature data. DFT calculations were also used to identify specific reactivity properties of NBBPA molecule based on the molecular orbital, charge distribution and electron density analysis, which indicated the reactive importance of carbonyl and NH2 groups, together with bromine atom. DFT calculations were also used for investigation of sensitivity of the NBBPA molecules towards the autoxidation mechanism, while molecular dynamics (MD) simulations were used to investigate the influence of water. The molecular docking results suggest that the compound might exhibit inhibitory activity against GyrB complex. [Display omitted] •FT-IR, FT-Raman, docking studies are reported.•Moderate antibacterial activity for the title compound.•Most reactive sites are predicted by using MEP plot.•Autoxidation and degradation properties are reported.•Exhibits inhibitory activity against GyrB complex.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2017.04.010