An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide: Synthesis and preliminary biological studies

Kevin L. Weiss, Galal Alshafie, Jason S. Chapman, Serena M. Mershon, Hussein Abou-Issa, Margaret Clagett-Dame, Robert W. Curley

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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.

Original languageEnglish
Pages (from-to)1583-1586
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume11
Issue number12
DOIs
StatePublished - Jun 18 2001
Externally publishedYes

Funding

Financial support in the form of a grant (CA49837) from the National Cancer Institute is gratefully acknowledged.

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