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-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 24
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.tetasy.2013.05.023
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.838-843
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.