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Benzoxazole is an aromatic organic compound having a benzene-fused oxazole ring structure, and an odor similar to pyridine. It is an important heterocyclic ring system which can either be isolated from natural products or accessed by total synthesis. Benzoxazoles can be considered as structural isosteres of the naturally occurring nucleic bases adenine and guanine, which allow them to interact easily with polymers of living systems.
The benzoxazole moiety is found in many biologically active compounds such as anticancer, antibacterial, antimicrobial, polycyclic and polyether antibiotics, antiparasites, anti-inflammatories, and anti convulsants. Furthermore, it is present in elastase inhibitors, whitening agents, polybenzoxazole polymers, synthetic heat resistant fibres, and optical bleaching agents. Benzoxazole has the ability to form complexes with double stranded DNA, which gives it an anti-cancer property and inhibits the enzyme mycobacterium tuberculosis Enoyl-ACP reductase, which prevents mycolic acid production, and in turn results in anti-tubercular activity. The 2-(2-arylphenyl)benzoxazole moiety has been found to be a new and selective ligand for the enzyme cyclooxygenase-2 (COX-2) (Seth, K., 2-(2-Arylphenyl)benzoxazole As a Novel Anti-Inflammatory Scaffold: Synthesis and Biological Evaluation, ACS Med. Chem. Lett., 2014, 5 (5), 512516).