Synthesis of an iminosugar based peptidomimetic analogue

被引：22

作者：

Chery, F ^{[1
]}

Murphy, PV ^{[1
]}

机构：

[1] Univ Coll Dublin, Conway Inst Biomol & Biomed Res, Dept Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 10期

关键词：

peptidomimetic; scaffold; deoxynojirimycin; azasugar; 1-deoxymannojirimycin; protease inhibitor;

D O I：

10.1016/j.tetlet.2004.01.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 1-deoxymannojirimycin based analogue of a known HIV-protease inhibitor is described. The strategies employed for introduction of the pharmocophore groups onto the azasugar scafford were based on regioselective reactions of the hydroxly groups of the natural product and of D-fructopyranoside derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2067 / 2069

页数：3

相关论文

共 31 条

[21]

Nicolaou K. C., 1990, PEPTIDES CHEM STRUCT, P881

[22] Novel synthesis of the glycosidase inhibitor deoxymannojirimycin and of a synthetic precursor D-lyxo-hexos-5-ulose [J].

O'Brien, JL ;

Tosin, M ;

Murphy, PV .

ORGANIC LETTERS, 2001, 3 (21) :3353-3356

[23]

OLSON GL, 1989, P BIOTECHNOL, P348

[24] DESIGN, SYNTHESIS, AND BINDING-AFFINITY OF A NONPEPTIDE MIMIC OF SOMATOSTATIN [J].

PAPAGEORGIOU, C ;

HALTINER, R ;

BRUNS, C ;

PETCHER, TJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (02) :135-140

[25] Carbohydrate-based scaffolds for the generation of sortiments of bioactive compounds [J].

Peri, F ;

Cipolla, L ;

Forni, E ;

Nicotra, F .

MONATSHEFTE FUR CHEMIE, 2002, 133 (04) :369-382

[26] Peptidomimetic design [J].

Ripka, AS ;

Rich, DH .

CURRENT OPINION IN CHEMICAL BIOLOGY, 1998, 2 (04) :441-452

[27] Carbohydrate-based small-molecule scaffolds for the construction of universal pharmacophore mapping libraries [J].

Sofia, MJ ;

Hunter, R ;

Chan, TY ;

Vaughan, A ;

Dulina, R ;

Wang, HM ;

Gange, D .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2802-2803

[28] A simple access to the D-mannosidase inhibitor, 1-deoxymannojirimycin [J].

Spreitz, J ;

Stütz, AE ;

Wrodnigg, TM .

CARBOHYDRATE RESEARCH, 2002, 337 (02) :183-186

[29] 6-guanidinopyranoses: Novel carbohydrate-based peptidomimetics [J].

Wessel, HP ;

Banner, D ;

Gubernator, K ;

Hilpert, K ;

Muller, K ;

Tschopp, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (07) :751-752

[30]

Wunberg T, 1998, ANGEW CHEM INT EDIT, V37, P2503, DOI 10.1002/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO

← 1 2 3 4 →