title: Preparation and biological activity of 13-substituted retinoic acids.
abstract: 13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity.
authors.affiliation: Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada, Kobe 658-8558, Japan. a-wada@kobepharma-u.ac.jp
authors.forename: Akimori
authors.initials: A
authors.lastname: Wada
authors.forename: Kouki
authors.initials: K
authors.lastname: Fukunaga
authors.forename: Masayoshi
authors.initials: M
authors.lastname: Ito
authors.forename: Yukari
authors.initials: Y
authors.lastname: Mizuguchi
authors.forename: Kimie
authors.initials: K
authors.lastname: Nakagawa
authors.forename: Toshio
authors.initials: T
authors.lastname: Okano
mesh_terms: D045744:Cell Line, Tumor; D005434:Flow Cytometry; D006801:Humans; D013057:Spectrum Analysis; D014212:Tretinoin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D014212:Tretinoin