C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene

J Med Chem. 2001 Dec 20;44(26):4688-95. doi: 10.1021/jm0103007.

Abstract

Nucleophilic additions of lithium keto and ester enolates and mono- and bifunctional Grignard reagents to artemisitene provided C-16-derived artemisinin monomers, dimers, trimers, and tetramers whose antimalarial and cytotoxic activities have been evaluated.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Artemisinins*
  • Cell Line
  • Chlorocebus aethiops
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Conformation
  • Plasmodium falciparum / drug effects
  • Polymers
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antimalarials
  • Antineoplastic Agents
  • Artemisinins
  • Polymers
  • Sesquiterpenes
  • artemisitene
  • artemisinin