Novel highly potent, structurally simple γ-trifluoromethyl γ-sulfone hydroxamate inhibitor of stromelysin-1 (MMP-3)

被引：36
|
作者：
Sani, M
Candiani, G
Pecker, F
Malpezzi, L
Zanda, M
机构：
[1] Politecn Milan, Dipartimento Chim Mat & Ingn Chim G Natta, I-20131 Milan, Italy
[2] CNR, Ist Chim Riconoscimento Mol, Sez A Quil, I-20131 Milan, Italy
[3] INSERM, U581, F-94010 Creteil, France
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 14期
关键词：
trifluoromethyl; matrix metalloproteinases; inhibitors; asymmetric synthesis;
D O I：
10.1016/j.tetlet.2005.02.063
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The gamma-trifluoromethyl gamma-sulfone hydroxamate 1 was synthesized both in racemic and enantiomerically pure forms by means of a thia-Michael reaction of p-methoxythiophenol on achiral and chiral 3,3,3-trifluorocrotonoyl Michael acceptors. The (R)-1 enantiomer was the most potent inhibitor of MMP-3 (stromelysin-1), showing an IC50 = 3.2 nM, as well as the most selective with respect to MMP-9 (65-fold). (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2393 / 2396
页数：4
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