An improved synthesis of the C-linked glucuronide of N-(4-hydroxyphenyl)retinamide.
Basic Information
ID: ALA1134907
Journal: Bioorg Med Chem Lett
Title: An improved synthesis of the C-linked glucuronide of N-(4-hydroxyphenyl)retinamide.
Authors: Walker JR, Alshafie G, Abou-Issa H, Curley RW.
Abstract: Retinoic acid analogues such as N-(4-hydroxyphenyl)retinamide (4-HPR) are effective chemopreventatives and chemotherapeutics for numerous types of cancer. The C-linked analogue of the O-glucuronide of 4-HPR (4-HPRCG) has been shown to be a more effective agent. The synthetic route to this molecule has been significantly improved by access to a key C-benzyl-glucuronide intermediate through employment of a Suzuki coupling reaction between an exoanomeric methylene sugar and an aryl bromide. Preliminary evidence shows 4-HPRCG has chemotherapeutic activity.
CiteXplore: 12161154
DOI: 10.1016/s0960-894x(02)00427-4
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