Preparation and biological activity of 13-substituted retinoic acids.
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.
Wada
Akimori
A
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
Fukunaga
Kouki
K
Ito
Masayoshi
M
Mizuguchi
Yukari
Y
Nakagawa
Kimie
K
Okano
Toshio
T
D045744:Cell Line, Tumor; D005434:Flow Cytometry; D006801:Humans; D013057:Spectrum Analysis; D014212:Tretinoin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*
D014212:Tretinoin