Total synthesis of a pepstatin analog incorporating two trifluoromethyl hydroxymethylene isosteres (Tfm-GABOB) and evaluation of Tfm-GABOB containing peptides as inhibitors of HIV-1 protease and MMP-9

被引：32

作者：

Pesenti, C

Arnone, A

Bellosta, S

Bravo, P

Canavesi, M

Corradi, E

Frigerio, M

Meille, SV

Monetti, M

Panzeri, W

Viani, F

Venturini, R

Zanda, M

机构：

[1] CNR, Ctr Studio Sostanze Organ Nat, I-20131 Milan, Italy

[2] CNR, CSSON, Dipartimento Chim, Politecn Milan, I-20131 Milan, Italy

[3] Univ Milan, Dipartimento Sci Farmaceut, I-20133 Milan, Italy

[4] Univ Trieste, Dipartimento Biochim Biofis & Chim Macromol, I-34127 Trieste, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 30期

关键词：

asymmetric synthesis; peptide isosteres; HIV; metalloproteinase; trifluoromethyl group;

D O I：

10.1016/S0040-4020(01)00543-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the asymmetric total synthesis of a trifluoromethyl (Tfm) analogue of the aspartate protease inhibitor pepstatin incorporating two gamma -Tfm-gamma -amino-beta -hydroxybutyric acid (gamma -Tfm-GABOB) units instead of the natural statine units. The title compound as well as several Tfm-substituted precursors were tested as inhibitors of HIV-1 protease and Gelatinase B (MMP-9) (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6511 / 6522

页数：12

共 49 条

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