Search for α-glucosidase inhibitors:: New N-substituted valienamine and conduramine F-1 derivatives

被引：51

作者：

Lysek, Robert

Schuetz, Catherine

Favre, Sylvain

O'Sullivan, Anthony C.

Pillonel, Christian

Kruelle, Thomas

Jung, Pierre M. J.

Clotet-Codina, Imma

Este, Jose A.

Vogel, Pierre ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Glycochim & Synth Asymetr, ISIC, BCH, CH-1015 Lausanne, Switzerland

[2] Syngenta AG, CH-4002 Basel, Switzerland

[3] Hosp Univ Germans Trias Pujol, Retrovirol Lab IrsiCaixa, E-08916 Badalona, Spain

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2006年 / 14卷 / 18期

关键词：

conduramine F-1 (aminoconduritol); alpha-glucosidase inhibitors; solid-phase synthesis; 'naked sugars'; imines; cytotoxicity;

D O I：

10.1016/j.bmc.2006.05.080

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (+/-)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward alpha-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6255 / 6282

页数：28

共 85 条

[1]

The synthetic development of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu®):: A challenge for synthesis & process research [J].