3-Hydroxy-4-methyl-5-pentyl-2-iminopyrrolidine: a potent and highly selective inducible nitric oxide synthase inhibitor

Bioorg Med Chem Lett. 2002 Nov 18;12(22):3337-9. doi: 10.1016/s0960-894x(02)00686-8.

Abstract

(3S,4S,5R)-2-Imino-4-methyl-5-pentyl-3-pyrrolidinol hydrochloride (1) is a potent inducible nitric oxide synthase (i-NOS) inhibitor that has three times the selectivity of its parent, (+)-cis-4-methyl-5-pentylpyrrolidin-2-imine hydrochloride (2).

Publication types

  • Comparative Study

MeSH terms

  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Imines / chemical synthesis
  • Imines / chemistry
  • Imines / pharmacology
  • Inhibitory Concentration 50
  • Isoenzymes / drug effects
  • Nitric Oxide Synthase / antagonists & inhibitors*
  • Nitric Oxide Synthase Type II
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 3-hydroxy-4-methyl-5-pentyl-2-iminopyrrolidine
  • 4-methyl-5-pentylpyrrolidin-2-imine
  • Enzyme Inhibitors
  • Imines
  • Isoenzymes
  • Pyrrolidines
  • NOS2 protein, human
  • Nitric Oxide Synthase
  • Nitric Oxide Synthase Type II