Synthesis and biological evaluation of analogues of M6G.

Claire Trécant, Alain Dlubala, Pascal George, Philippe Pichat, Isabelle Ripoche, Yves Troin

Clermont Université, ENSCCF, EA 987, LCHG, BP 10448, F-63000 Clermont-Ferrand, France.

European journal of medicinal chemistry 2011 Sep

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Synthesis and biological evaluation of new derivatives of Morphine-6-Glucuronide (M6G) are described. M6G is an active metabolite of morphine which displays more analgesia than morphine with a superior side effect profile but with a less efficiently BBB penetration. These phenomena could be explained by the presence of the glucuronide moiety, which confers a higher hydrophilic character compare to morphine. In this context, we have prepared three analogues of M6G possessing a tetrazole, an oxadiazole, and a triazolopyrimidine moiety instead of the carboxylic acid function on position 5 of the sugar. These three analogues showed higher analgesic properties than morphine and M6G even by oral administration. Copyright © 2011 Elsevier Masson SAS. All rights reserved.

Citation

Claire Trécant, Alain Dlubala, Pascal George, Philippe Pichat, Isabelle Ripoche, Yves Troin. Synthesis and biological evaluation of analogues of M6G. European journal of medicinal chemistry. 2011 Sep;46(9):4035-41