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

Date

2013-07-31

Author

Ayan, Seylan
Doğan, Özdemir
Ivantcova, Polina M.
Datsuk, Nikita G.
Shulga, Dmitry A.
Chupakhin, Vladimir I.
Zabolotnev, Dmitry V.
Kudryavtsev, Konstantin V.

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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.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/41975

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2013.05.023

Collections

Department of Chemistry, Article

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Citation Formats

S. Ayan et al., “Asymmetric synthesis and molecular docking study of enantiomerically pure pyrrolidine derivatives with potential antithrombin activity,” TETRAHEDRON-ASYMMETRY, pp. 838–843, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41975.