Second generation tetrahydroquinoline-based protein farnesyltransferase inhibitors as antimalarials

J Med Chem. 2007 Sep 20;50(19):4585-605. doi: 10.1021/jm0703340. Epub 2007 Aug 28.

Abstract

Substituted tetrahydroquinolines (THQs) have been previously identified as inhibitors of mammalian protein farnesyltransferase (PFT). Previously we showed that blocking PFT in the malaria parasite led to cell death and that THQ-based inhibitors are the most potent among several structural classes of PFT inhibitors (PFTIs). We have prepared 266 THQ-based PFTIs and discovered several compounds that inhibit the malarial enzyme in the sub- to low-nanomolar range and that block the growth of the parasite (P. falciparum) in the low-nanomolar range. This body of structure-activity data can be rationalized in most cases by consideration of the X-ray structure of one of the THQs bound to mammalian PFT together with a homology structural model of the malarial enzyme. The results of this study provide the basis for selection of antimalarial PFTIs for further evaluation in preclinical drug discovery assays.

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Binding Sites
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Farnesyltranstransferase / antagonists & inhibitors*
  • Farnesyltranstransferase / chemistry
  • Models, Molecular
  • Molecular Structure
  • Plasmodium falciparum / drug effects*
  • Plasmodium falciparum / enzymology
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Quinolines / pharmacology
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Quinolines
  • Farnesyltranstransferase