Synthesis and acrosin inhibitory activities of 5-phenyl-1H-pyrazole-3-carboxylic acid amide derivatives

Bioorg Med Chem Lett. 2013 Jul 15;23(14):4177-84. doi: 10.1016/j.bmcl.2013.05.031. Epub 2013 May 22.

Abstract

A series of novel 5-phenyl-1H-pyrazole-3-carboxylic acid amide derivatives were designed, synthesized, and their acrosin inhibitory activities in vitro were evaluated. The results of the acrosin inhibitory activity showed that all target compounds were more potent than control TLCK. Compounds AQ-A1, AQ-D3, AQ-D4, AQ-E4 and AQ-E5 exhibited stronger acrosin inhibitory activities than control ISO-1. Especially, compound AQ-E5 displayed the most potent acrosin inhibitory activity in all the compounds, with an IC50 of 0.01μmol/mL. This study provided a new structural class for the development of novel acrosin inhibitory agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrosin / antagonists & inhibitors
  • Acrosin / metabolism
  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / pharmacokinetics
  • Binding Sites
  • Catalytic Domain
  • Crystallography, X-Ray
  • Half-Life
  • Humans
  • Molecular Conformation
  • Molecular Docking Simulation
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacokinetics
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacokinetics

Substances

  • AQ-E5 compound
  • Amides
  • Protease Inhibitors
  • Pyrazoles
  • pyrazole
  • Acrosin