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Published on: January 3, 2018
An improved synthesis of the C-linked glucuronide of N-(4-hydroxyphenyl)retinamide
Joel R Walker1, Galal Alshafie, Hussein Abou-Issa
1Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus 43210, USA.
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.
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