Synthesis of betulinic acid acyl glucuronide for application in anticancer prodrug monotherapy

被引：45

作者：

Gauthier, Charles ^{[1
]}

Legault, Jean ^{[1
]}

Rondeau, Simon ^{[1
]}

Pichette, Andre ^{[1
]}

机构：

[1] Univ Quebec Chicoutimi, Lab LASEVE, Chaire Rech Agents Anticancereux Origine Nat, Chicoutimi, PQ G7H 2B1, Canada

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 09期

关键词：

METHYL ACETYL DERIVATIVES; 1-BETA-O-ACYL GLUCURONIDES; BIOLOGICAL-ACTIVITY; SELECTIVE ACYLATION; BETA-GLUCURONIDASE; ENZYMATIC REMOVAL; PROTECTING GROUPS; DRUG; REACTIVITY; CANDIDATE;

D O I：

10.1016/j.tetlet.2008.12.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

The synthesis of 28-O-beta-D-glucuronide betulinic acid, an acyl glucuronide derivative, was successfully carried out for the first time using commercially available peracetylated methyl glucuronate bromide under phase-transfer conditions. The target compound could be used in an anticancer prodrug monotherapy (PMT) strategy since it is non-cytotoxic, non-haemolytic, more water soluble than betulinic acid, it possesses a good in vitro stability in phosphate buffer and can be hydrolyzed in the presence of beta-D-glucuronidase releasing in vitro betulinic acid, a promising anticancer agent. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：988 / 991

页数：4

共 33 条

[1]

An improved chemo-enzymatic synthesis of 1-β-o-acyl glucuronides:: Highly chemoselective enzymatic removal of protecting groups from corresponding methyl acetyl derivatives [J].