Tetrahydrofuran as a scaffold for peptidomimetics. Application to the design and synthesis of conformationally constrained metalloproteinase inhibitors

被引：24

作者：

Hanessian, S ^{[1
]}

Moitessier, N ^{[1
]}

Wilmouth, S ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

TETRAHEDRON | 2000年 / 56卷 / 39期

基金：

加拿大自然科学与工程研究理事会;

关键词：

peptide mimetics; enzyme inhibitors; molecular modeling; stereocontrol;

D O I：

10.1016/S0040-4020(00)00687-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure functionalized tetrahydrofurans were synthesized as prototypical conformationally constrained analogs of acyclic succinic acid-based inhibitors of metalloproteinases. While preliminary docking study showed good congruence with a potent inhibitor, the biological results were disappointing. Molecular dynamics simulation revealed the weakness of the H-bond interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7643 / 7660

页数：18

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