Discovery of a novel class of orally active trypanocidal N-myristoyltransferase inhibitors

J Med Chem. 2012 Jan 12;55(1):140-52. doi: 10.1021/jm201091t. Epub 2011 Dec 7.

Abstract

N-Myristoyltransferase (NMT) represents a promising drug target for human African trypanosomiasis (HAT), which is caused by the parasitic protozoa Trypanosoma brucei. We report the optimization of a high throughput screening hit (1) to give a lead molecule DDD85646 (63), which has potent activity against the enzyme (IC(50) = 2 nM) and T. brucei (EC(50) = 2 nM) in culture. The compound has good oral pharmacokinetics and cures rodent models of peripheral HAT infection. This compound provides an excellent tool for validation of T. brucei NMT as a drug target for HAT as well as a valuable lead for further optimization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyltransferases / antagonists & inhibitors*
  • Administration, Oral
  • Aminopyridines / chemical synthesis*
  • Aminopyridines / pharmacokinetics
  • Aminopyridines / pharmacology
  • Animals
  • Cell Line
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Databases, Factual
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Parasitic Sensitivity Tests
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / pharmacology
  • Trypanocidal Agents / chemical synthesis*
  • Trypanocidal Agents / pharmacokinetics
  • Trypanocidal Agents / pharmacology
  • Trypanosoma brucei brucei / drug effects
  • Trypanosomiasis, African / drug therapy

Substances

  • Aminopyridines
  • DDD 85646
  • Sulfonamides
  • Trypanocidal Agents
  • Acyltransferases
  • glycylpeptide N-tetradecanoyltransferase

Associated data

  • PDB/3H5Z
  • PDB/4A2Z
  • PDB/4A30
  • PDB/4A31
  • PDB/4A32
  • PDB/4A33