Asymmetric synthesis and molecular docking study of enantiomerically pure pyrrolidine derivatives with potential antithrombin activity |
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Authors: | Seylan Ayan Özdemir Dogan Polina M. Ivantcova Nikita G. Datsuk Dmitry A. Shulga Vladimir I. Chupakhin Dmitry V. Zabolotnev Konstantin V. Kudryavtsev |
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Affiliation: | 1. Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey;2. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia;3. Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka 142432, Moscow region, Russia |
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Abstract: | 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. |
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