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Facile Synthesis and In Vitro Nitric Oxide Production Inhibitory Activity of Benzoxazoles
Author(s) -
Park Hyeong Jin,
Kim JinKyung,
Jun JongGab
Publication year - 2018
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11465
Subject(s) - nitric oxide , in vitro , chemistry , demethylation , cytotoxicity , inhibitory postsynaptic potential , ic50 , nuclear chemistry , stereochemistry , organic chemistry , biochemistry , biology , endocrinology , gene expression , dna methylation , gene
A Facile synthesis of natural benzoxazoles, nocarbenzoxazoles F ( 1 ), G ( 5 ) and their derivatives ( 2–4 and 6 – 8) was achieved from the commercially available inexpensive precursors with overall yields ranging from 15 to 49%. Our strategy to access this family of benzoxazoles was enabled by POCl 3 ‐mediated cyclodehydration, selective and/or complete demethylation and reduction as the key steps. Their in vitro nitric oxide (NO) inhibitory effect was further evaluated as an indicator of anti‐inflammatory activity in LPS‐induced RAW 264.7 cells and found to display weak to moderate activity in a concentration‐dependent manner without marked cytotoxicity. Overall, compound 8 (53.5% at 10 μM; IC 50 = 8.17 μM) followed by compound 6 (12.7% at 10 μM; IC 50 = 28.26 μM) exhibited significant activity, being more active than the positive control, L‐NMMA (19.5% at 10 μM; IC 50 = 18.77 μM).