Journal
CHEMISTRY & BIODIVERSITY
Volume 19, Issue 10, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbdv.202200489
Keywords
benzoxazole; anti-inflammatory; cytotoxicity; molecular docking
Funding
- CSIR, New Delhi [09/752(0097)/2019-EMR-I]
- HSCST, Chandigarh
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Synthesized 2-halogenatedphenyl benzoxazole-5-carboxylic acids showed significant anti-inflammatory and cytotoxic activities, with compound 6b exhibiting comparable anti-inflammatory activity to standard drug ibuprofen and compound 6c showing superior cytotoxic activity to doxorubicin against human prostate carcinoma epithelial cell lines.
2-Halogenatedphenyl benzoxazole-5-carboxylic acids with mono-halogen (chloro, bromo and fluoro) substituted at ortho-, meta- and para-positions on the phenyl ring were designed and synthesized based on significance of presence of halogen in increasing number of marketed halogenated drugs and importance of benzoxazoles. These 2-alogenatedphenylbenzoxazole-5-carboxylic acids and their methyl esters were screened for anti-inflammatory activity, and cytotoxicity. 2-(3-Chlorophenyl)benzoxaole-5-carboxylic acid (6b) exhibited significant anti-inflammatory activity with IC50 values of 0.103 mM almost equivalent to the standard drug ibuprofen (0.101 mM). 2-(4-Chlorophenyl)benzoxaole-5-carboxylic acid (6c) showed excellent cytotoxic activity against 22Rv1 cells (human prostate carcinoma epithelial cell lines) with IC50 value of 1.54 mu M better than that of standard drug doxorubicin having IC50 value of 2.32 mu M. More importantly, the selectivity index of this potential molecule was found to be 57.74. Molecular docking analysis resulted in good binding interactions of these compounds with their respective biochemical targets viz. Cyclooxygenase-2 and aldo-keto reductase IC3.
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