Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity

Bioorg Med Chem. 2003 Oct 1;11(20):4417-22. doi: 10.1016/s0968-0896(03)00491-7.

Abstract

The previously unknown antiplasmodial activity of the plant derived natural product totarol is reported. Novel beta-amino alcohol derivatives based on this natural product were designed, synthesised and evaluated for in vitro antiplasmodial activity and cytotoxicity. These derivatives showed antiplasmodial IC50 values in the range of 0.6-3.0 microM and were equally active against a chloroquine-sensitive and resistant strain of Plasmodium falciparum, while showing little cytotoxicity against a mammalian cell line (CHO). In terms of lead development, two of the compounds based on substituted phenylpiperazine warrant further investigation as potential antiplasmodial leads. In addition to their selective antiplasmodial activity and lack of chloroquine cross-resistance, these compounds are structurally different to any of the available antimalarial drugs.

MeSH terms

  • Abietanes
  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / pharmacology
  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / pharmacology
  • CHO Cells
  • Cell Survival / drug effects
  • Chloroquine
  • Cricetinae
  • Diterpenes / chemical synthesis*
  • Diterpenes / pharmacology
  • Drug Design
  • Drug Resistance
  • Inhibitory Concentration 50
  • Plasmodium falciparum / drug effects*

Substances

  • Abietanes
  • Amino Alcohols
  • Antimalarials
  • Diterpenes
  • totarol
  • Chloroquine