1H-1,2,3-Triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates: synthesis and antimalarial evaluation

Bioorg Med Chem Lett. 2014 Feb 1;24(3):756-9. doi: 10.1016/j.bmcl.2013.12.109. Epub 2014 Jan 3.

Abstract

A series of 1H-1,2,3-triazole-tethered isatin-7-chloroquinoline and 3-hydroxy-indole-7-chloroquinoline conjugates have been synthesized and evaluated for their antimalarial activity against chloroquine-resistant W2 strain of Plasmodium falciparum. The most potent of the test compound with an optimum combination of 3-hydroxy-indole ring and a n-butyl linker displayed an IC50 value of 69 nM.

Keywords: 1H-1,2,3-Triazole; 3-Hydroxy-indole-2-one; 7-Chloroquinoline; Antimalarial activity; Isatin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Antimalarials / pharmacology*
  • Chloroquine / chemical synthesis
  • Chloroquine / chemistry
  • Chloroquine / pharmacology
  • Drug Resistance
  • Hydrazines / chemical synthesis*
  • Hydrazines / chemistry
  • Hydrazines / pharmacology*
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology
  • Inhibitory Concentration 50
  • Isatin / chemical synthesis
  • Isatin / chemistry
  • Isatin / pharmacology
  • Plasmodium falciparum / drug effects*
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology

Substances

  • Antimalarials
  • Hydrazines
  • Indoles
  • Quinolines
  • Triazoles
  • Isatin
  • indole
  • Chloroquine