title: Structure-activity relationship study on benzoic acid part of diphenylamine-based retinoids.
abstract: Based on structure-activity relationship studies of the benzoic acid part of diphenylamine-based retinoids, the potent RXR agonist 4 was derivatized to obtain retinoid agonists, synergists, and an antagonist. Cinnamic acid derivatives 5 and phenylpropionic acid derivatives 6 showed retinoid agonistic and synergistic activities, respectively. The difference of the activities is considered to be due to differences in the flexibility of the carboxylic acid-containing substituent on the diphenylamine skeleton. Compound 7, bearing a methyl group at the meta position to the carboxyl group, was an antagonist, dose-dependently inhibiting HL-60 cell differentiation induced by 3.3 × 10(-10)M Am80.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Kiminori
authors.initials: K
authors.lastname: Ohta
authors.forename: Emiko
authors.initials: E
authors.lastname: Kawachi
authors.forename: Koichi
authors.initials: K
authors.lastname: Shudo
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kagechika
mesh_terms: D019817:Benzoic Acid / Q000737:chemistry*; D002454:Cell Differentiation / Q000187:drug effects; D002934:Cinnamates / Q000737:chemistry; D004159:Diphenylamine / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D010666:Phenylpropionates / Q000737:chemistry; D047488:Retinoid X Receptors / Q000819:agonists / Q000037:antagonists & inhibitors / Q000378:metabolism; D012176:Retinoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D002934:Cinnamates; D010666:Phenylpropionates; D047488:Retinoid X Receptors; D012176:Retinoids; C029010:cinnamic acid; D019817:Benzoic Acid; D004159:Diphenylamine