- Synthesis and biological evaluation of analogues of M6G.
Synthesis and biological evaluation of analogues of M6G.
European journal of medicinal chemistry (2011-06-22)
Claire Trécant, Alain Dlubala, Pascal George, Philippe Pichat, Isabelle Ripoche, Yves Troin
PMID21689868
要旨
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.