An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide. synthesis and preliminary biological studies.
The synthesis of a nonhydrolyzable, carbon-linked analogue (4-HBR) of the retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) using Umpolung methods is described. Preliminary studies of biological activity show 4-HBR is similar to 4-HPR in its actions although a potentially relevant and desirable difference is its reduced suppression of plasma vitamin A levels. These results show that 4-HPR does not have to be hydrolyzed to retinoic acid to produce its chemotherapeutic effects.
Weiss
K L
KL
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.
Alshafie
G
G
Chapman
J S
JS
Mershon
S M
SM
Abou-Issa
H
H
Clagett-Dame
M
M
Curley
R W
RW
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000493:pharmacokinetics* / Q000494:pharmacology; D001711:Biotransformation; D005260:Female; D017313:Fenretinide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics* / Q000494:pharmacology; D006868:Hydrolysis; D008325:Mammary Neoplasms, Experimental / Q000188:drug therapy; D051381:Rats; D014801:Vitamin A / Q000097:blood
D000970:Antineoplastic Agents; D014801:Vitamin A; D017313:Fenretinide