Synthesis and aromatase inhibitory evaluation of 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives

Bioorg Med Chem. 2016 Oct 1;24(19):4723-4730. doi: 10.1016/j.bmc.2016.08.014. Epub 2016 Aug 10.

Abstract

In this paper, 13 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives were synthesized and their aromatase inhibitory activities were measured. The results show that the substitution of the groups on benzyl group can further improve their bioactivity and the compound with Cl on the para position of benzyl has the highest bioactivity (IC50=9.02nM). A QSAR model was constructed from the 13 compounds with genetic function approximation using DS 2.1 package. This model can explain 90.09% of the variance (R(2)Adj), while it can predict 84.95% of the variance (R(2)cv) with the confidence interval of 95%.

Keywords: 4-N-Nitrophenyl substituted amino-4H-1,2,4-triazole; Aromatase inhibitors; QSAR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aromatase / metabolism*
  • Aromatase Inhibitors / chemical synthesis
  • Aromatase Inhibitors / chemistry*
  • Aromatase Inhibitors / pharmacology*
  • Humans
  • Nitrophenols / chemical synthesis
  • Nitrophenols / chemistry
  • Nitrophenols / pharmacology
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / pharmacology*

Substances

  • Aromatase Inhibitors
  • Nitrophenols
  • Triazoles
  • 4-nitrophenyl
  • 1,2,4-triazole
  • Aromatase
  • CYP19A1 protein, human