title: Catechol O-methyltransferase. 10. 5-Substituted 3-hydroxy-4-methoxybenzoic acids (isovanillic acids) and 5-substituted 3-hydroxy-4-methoxybenzaldehydes (isovanillins) as potential inhibitors.
abstract: A series of 5-substituted 3-hydroxy-4-methoxybenzoic acids (isovanillic acids) and -benzaldehydes (isovanillins) have been synthesized and evaluated as inhibitors of rat liver catechol O-methyltransferase. The compounds exhibited either noncompetitive or competitive patterns of inhibition when 3,4-dihydroxybenzoic acid was the variable substrate. The benzaldehydes were significantly more potent inhibitors than the corresponding benzoic acids, and electron-withdrawing substituents in the 5 position greatly enhanced their inhibitory activity.
mesh_terms: D000818:Animals; D065098:Catechol O-Methyltransferase Inhibitors; D055598:Chemical Phenomena; D002621:Chemistry; D005421:Flavoring Agents / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D062385:Hydroxybenzoates / Q000138:chemical synthesis*; D066298:In Vitro Techniques; D007700:Kinetics; D008099:Liver / Q000201:enzymology; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D014641:Vanillic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D065098:Catechol O-Methyltransferase Inhibitors; D005421:Flavoring Agents; D062385:Hydroxybenzoates; D014641:Vanillic Acid