Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine

  • ACS Med Chem Lett. 2013 May 22;4(7):637-41. doi: 10.1021/ml400164t.
Peter M Njogu  1 ,  Jiri Gut  2 ,  Philip J Rosenthal  2 ,  Kelly Chibale  3
Affiliations
  • 1. Department of Chemistry, University of Cape Town , Rondebosch 7701, South Africa.
  • 2. Department of Medicine, San Francisco General Hospital, University of California , San Francisco, California 94143, United States.
  • 3. Department of Chemistry, University of Cape Town , Rondebosch 7701, South Africa ; Institute of Infectious Disease and Molecular Medicine, University of Cape Town , Rondebosch 7701, South Africa.
PMID: 24900723 DOI: 10.1021/ml400164t
Abstract

A series of hybrid compounds based on (2R,3S)-N-benzoyl-3-phenylisoserine, artemisinin, and quinoline moieties was synthesized and tested for in vitro antiplasmodial activity against erythrocytic stages of K1 and W2 strains of Plasmodium falciparum. Two hybrid compounds incorporating (2R,3S)-N-benzoyl-3-phenylisoserine and artemisinin scaffolds were 3- to 4-fold more active than dihydroartemisinin, with nanomolar IC50 values against Plasmodium falciparum K1 strain.

Keywords
(2R,3S)-N-Benzoyl-3-phenylisoserine; antiplasmodial activity; artemisinin; hybrids; quinoline.