4-substituted indazoles as new inhibitors of neuronal nitric oxide synthase

Bioorg Med Chem Lett. 2007 Jun 1;17(11):3177-80. doi: 10.1016/j.bmcl.2007.03.024. Epub 2007 Mar 14.


A series of halo-1-H-indazoles has been synthesized and evaluated for its inhibitory activity on neuronal nitric oxide synthase. Introduction of bromine at the C4 position of the indazole ring system provided a compound almost as potent as the reference compound, that is, 7-nitroindazole (7-NI). The importance of position 4 is further demonstrated by the synthesis and pharmacological evaluation of the 4-nitroindazole which was also a potent inhibitor of NOS activity. These compounds also exhibited in vivo NOS inhibitory activity, as attested by potent antinociceptive effects following systemic administration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bromine / chemistry
  • Cerebellum / cytology
  • Cerebellum / drug effects
  • Cerebellum / enzymology
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Indazoles / chemical synthesis
  • Indazoles / chemistry*
  • Indazoles / pharmacology*
  • Neurons / drug effects
  • Neurons / enzymology
  • Nitric Oxide Synthase Type I / antagonists & inhibitors*
  • Rats
  • Structure-Activity Relationship


  • Enzyme Inhibitors
  • Indazoles
  • Nitric Oxide Synthase Type I
  • Bromine
  • 7-nitroindazole