Synthesis and pharmacological activity of 6-[(E)-2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids.
6-[(E)-2-(2,6,6-Trimethyl-1-cyclohexen-1-yl)ethen-1-yl]- and 6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids (4 and 8) have been synthesized and show significant activity in reversing the keratinization process in hamster tracheal organ culture and in inhibiting the induction of ornithine decarboxylase in mouse skin by 12-O-tetradecanoylphorbol-13-acetate, two assays used to measure retinoid activity. The 2-naphthalenecarboxylic acid 8 was more active than 4.
D000818:Animals; D001681:Biological Assay; D006224:Cricetinae; D004790:Enzyme Induction; D007202:Indicators and Reagents; D007633:Keratins / Q000378:metabolism; D051379:Mice; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology; D009924:Organ Culture Techniques; D009955:Ornithine Decarboxylase / Q000235:genetics; D012867:Skin / Q000187:drug effects / Q000201:enzymology; D013329:Structure-Activity Relationship; D013755:Tetradecanoylphorbol Acetate / Q000633:toxicity; D014132:Trachea / Q000187:drug effects
D007202:Indicators and Reagents; D009281:Naphthalenes; D007633:Keratins; C039574:6-(2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethen-1-yl)-2-naphthalenecarboxylic acid; C039575:6-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acid; D009955:Ornithine Decarboxylase; D013755:Tetradecanoylphorbol Acetate