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

Ayan S., DOĞAN Ö. , Ivantcova P. M. , Datsuk N. G. , Shulga D. A. , Chupakhin V. I. , ...Daha Fazla

TETRAHEDRON-ASYMMETRY, cilt.24, ss.838-843, 2013 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 24
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.tetasy.2013.05.023
  • Sayfa Sayıları: ss.838-843


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.