Synthesis of 2-phenylisothiazol-3(2H)-one 1,1-dioxides: Inhibitors of human leukocyte elastase

被引：0

作者：

Gütschow, Michael ^{[1
]}

Pietsch, Markus ^{[1
]}

Taubert, Kathleen ^{[2
]}

Freysoldt, Tonia H. E. ^{[2
]}

Schulze, Bärbel ^{[2
]}

机构：

[1] Pharmazeutisches Institut, Poppelsdorf, Universität Bonn, D-53115 Bonn

[2] Institut für Organische Chemie, Universität Leipzig, D-04103 Leipzig

来源：

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences | 2003年 / 58卷 / 01期

关键词：

Enzyme Inhibition; Human Leukocyte Elastase; Sultams;

D O I：

10.1515/znb-2003-0115

中图分类号：

学科分类号：

摘要：

A series of 2-phenylisothiazol-3(2H)-one 1,1-dioxides 14a-q were synthesized by oxidation of isothiazolium perchlorates 12. The inhibition of the serine proteases cathepsin G, chymotrypsin and human leukocyte elastase (HLE) by 14 was investigated. Some 4,5-diphenyl substituted derivatives (14i-k) were found to inhibit HLE in a time-dependent manner and exhibited kobs/[I] values > 500 M-1s-1. 14k (kobs/[I] = 2400 M-1s-1), was the most potent HLE inhibitor of this series. Kinetic investigations led to the conclusion that 2-phenylisothiazol-3(2H)-one 1,1-dioxides interact with HLE at the active site as well as at another binding site, resulting in a complex type of inhibition.

引用

页码：111 / 120

页数：9

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