Various approaches to the synthesis of 2-aryl-6-substituted benzoxazoles are described. The products, which included the 6-methyl derivative 4a, ethylamines 10 and 19, ethanols 12 and 14, the acetic and alpha-methylacetic acids 9 and 16a--f, and the acetic ester 11, were screened for antiinflammatory activity on the carrageenan-induced rat paw edema test. Some of the compounds possessed activity superior to that of phenylbutazone and of the same order as that of benoxaprofen.
The syntheses of eight of the title compounds are described. The compounds possessed activity comparable with that of the previously tested 2-substituted phenyl analogs in the carrageenan-induced rat paw edema test.
4- and 7-benzoxazoleacetic and alpha-methylacetic acids substituted in the 2 position with phenyl and substituted phenyl groups have been synthesized and tested on the carrageenan-induced rat paw edema assay. The only compound found to have significant activity, albeit of a low order, was 2-phenyl-alpha-methyl-7-benzoxazoleacetic acid.
The synthesis of alpha-methyl-5-benzimidazoleacetic acid (17), its 2-amino, 2-phenyl, 2-(4-chlorophenyl), and 2-(4-chlorophenyl)-1-methyl derivatives (18,4,3, and 5, respectively), and alpha-methyl-2-oxo-2,3-dihydro-5-benzimidazoleacetic acid (19) is described. None of the compounds were effective in reducing carrageenan-induced edema in rat paws.
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