Design, synthesis and biological evaluation of imidazole and triazole-based carbamates as novel aromatase inhibitors

Eur J Med Chem. 2021 Feb 5:211:113115. doi: 10.1016/j.ejmech.2020.113115. Epub 2020 Dec 25.

Abstract

In the search for novel aromatase inhibitors, a series of triazole and imidazole-based carbamate derivatives were designed and synthesized. Final compounds were thus evaluated against human aromatase by in vitro kinetic experiments in a fluorimetric assay in comparison with letrozole. The effect of most active derivatives 13a and 15c was then evaluated in vitro on the human breast cancer cell line MCF7 by MTT assay, cytotoxicity assay (LDH release) and cell cycle analysis, revealing a dose-dependent inhibition profile of cell viability and low micromolar IC50 values. In addition, docking simulations were also carried out to elucidate at a molecular level of detail the binding modes adopted to target human aromatase.

Keywords: Aromatase inhibitors; Breast cancer; Carbamates; Cytochrome P450; Imidazole; Triazole.

MeSH terms

  • Aromatase Inhibitors / chemical synthesis*
  • Aromatase Inhibitors / pharmacology
  • Aromatase Inhibitors / therapeutic use*
  • Carbamates / chemical synthesis*
  • Carbamates / pharmacology
  • Carbamates / therapeutic use*
  • Drug Design
  • Humans
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacology
  • Imidazoles / therapeutic use*
  • Molecular Structure
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology
  • Triazoles / therapeutic use*

Substances

  • Aromatase Inhibitors
  • Carbamates
  • Imidazoles
  • Triazoles