Parallel synthesis of potent, pyrazole-based inhibitors of Helicobacter pylori dihydroorotate dehydrogenase

J Med Chem. 2002 Oct 10;45(21):4669-78. doi: 10.1021/jm020112w.

Abstract

The identification of several potent pyrazole-based inhibitors of bacterial dihydroorotate dehydrogenase (DHODase) via a directed parallel synthetic approach is described below. The initial pyrazole-containing lead compounds were optimized for potency against Helicobacter pylori DHODase. Using three successive focused libraries, inhibitors were rapidly identified with the following characteristics: K(i) < 10 nM against H. pylori DHODase, sub-microg/mL H. pylori minimum inhibitory concentration activity, low molecular weight, and >10 000-fold selectivity over human DHODase.

MeSH terms

  • Combinatorial Chemistry Techniques
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Helicobacter pylori / drug effects*
  • Helicobacter pylori / enzymology
  • Humans
  • Oxidoreductases / antagonists & inhibitors*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Pyrazoles
  • Oxidoreductases
  • dehydroorotate dehydrogenase