Inhibitors of type I MetAPs containing pyridine-2-carboxylic acid thiazol-2-ylamide. Part 1: SAR studies on the determination of the key scaffold

Bioorg Med Chem Lett. 2005 Feb 1;15(3):635-8. doi: 10.1016/j.bmcl.2004.11.034.

Abstract

Systematic SAR studies on the HTS hit pyridine-2-carboxylic acid thiazol-2-ylamide (PACT) analogues revealed that the scaffold of PCAT is indispensable for the inhibition of type I MetAP. For effective inhibition of the enzyme, the most suitable position to modify is the 3-position of the pyridine ring of PCAT, and the best substituents are those containing O or N atoms connected directly with the pyridine ring. These findings provide useful information for the design and discovery of more potent inhibitors of type I MetAPs.

Publication types

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

MeSH terms

  • Amides / chemistry*
  • Amides / pharmacology
  • Aminopeptidases / antagonists & inhibitors*
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology
  • Bacterial Proteins / antagonists & inhibitors
  • Escherichia coli / enzymology
  • Humans
  • Inhibitory Concentration 50
  • Methionyl Aminopeptidases
  • Pyridines / chemical synthesis
  • Pyridines / pharmacology
  • Salmonella typhimurium / enzymology
  • Structure-Activity Relationship
  • Thiazoles / chemistry*
  • Thiazoles / pharmacology
  • Thioamides / chemical synthesis*
  • Thioamides / pharmacology

Substances

  • Amides
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Bacterial Proteins
  • Pyridines
  • Thiazoles
  • Thioamides
  • pyridine-2-carboxylic acid thiazol-2-ylamide
  • Aminopeptidases
  • Methionyl Aminopeptidases