Aromatic retinoic acid analogs. 2. Synthesis and pharmacological activity

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Abstract
Aromatic analogs of (E)-1-(4-carboxyphenyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)butadiene and its ethyl ester were synthesized as potential chemopreventive agents for the treatment of epithelial cancer and such skin diseases as psoriasis and cystic acne. The phenyl ring was replaced by 2-fluorophenyl, 2-methoxyphenyl, thienyl, furanyl and pyridyl groups. The 1-fluorobutadiene analog was also synthesized. With exception for the furanyl analog, these compounds demonstrated good activity in reversing keratinization in hamster tracheal organ culture and in inhibiting the induction of ornithine decarboxylase in mouse epidermis by a tumor promoter.