Asymmetric synthesis and molecular docking study of enantiomerically pure pyrrolidine derivatives with potential antithrombin activity

被引：15

作者：

Ayan, Seylan ^{[1
]}

Dogan, Ozdemir ^{[1
]}

Ivantcova, Polina M. ^{[2
]}

Datsuk, Nikita G. ^{[2
]}

Shulga, Dmitry A. ^{[2
]}

Chupakhin, Vladimir I. ^{[2
]}

Zabolotnev, Dmitry V. ^{[2
]}

Kudryavtsev, Konstantin V. ^{[2
,3
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06800 Ankara, Turkey

[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

[3] Russian Acad Sci, Inst Physiol Act Cpds, Chernogolovka 142432, Moscow Region, Russia

来源：

TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 13-14期

基金：

俄罗斯基础研究基金会;

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; RATIONAL DRUG DESIGN; AZOMETHINE YLIDES; SCHIFF-BASES; COMPLEXES; NITROALKENES; THROMBIN; ACIDS; NITROOLEFINS; INHIBITORS;

D O I：

10.1016/j.tetasy.2013.05.023

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The (2R,4R,5S)- and (2S,4S,5R)-enantiomers of 4-(tert-butyl) 2-methyl 5-(4-bromophenyl)-pyrrolidine-2,4-dicarboxylate 3 were synthesized efficiently with an ee of >90% on a gram scale using a FAM-catalytic methodology. Subsequent modification afforded enantiopure N-((4-chlorophenyl)thio)acetyl pyrrolidine derivatives 4, which are potential thrombin inhibitors according to comprehensive molecular docking studies. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：838 / 843

页数：6

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