title: An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide. synthesis and preliminary biological studies.
abstract: 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.
authors: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.
authors: K L
authors: KL
authors: Weiss
authors: G
authors: G
authors: Alshafie
authors: J S
authors: JS
authors: Chapman
authors: S M
authors: SM
authors: Mershon
authors: H
authors: H
authors: Abou-Issa
authors: M
authors: M
authors: Clagett-Dame
authors: R W
authors: RW
authors: Curley
mesh_terms: 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
chemical_list: D000970:Antineoplastic Agents; D014801:Vitamin A; D017313:Fenretinide