6-[(4-Fluorophenyl)(1H-imidazol-1-yl)methyl]-1,3-benzodioxol-5-ol and 6-[(4-methoxyphenyl)(1H-imidazol-1-yl)methyl]-1,3-benzodioxol-5-ol

Acta Crystallogr C. 2010 Oct;66(Pt 10):o499-502. doi: 10.1107/S0108270110034773. Epub 2010 Sep 10.

Abstract

The title compounds, C(17)H(13)FN(2)O(3) and C(18)H(16)N(2)O(4), are new potent aromatase inhibitors combining the common features of second- and third-generation nonsteroid anti-aromatase compounds. The molecules have a propeller shape, with dihedral angles between adjacent planes in the range 49-86°. A quantum mechanical ab initio Roothaan-Hartree-Fock calculation for the isolated molecules shows values for these angles close to the ideal value of 90°. Docking studies of the molecules in the aromatase substrate show that their strong inhibitor potency can be attributed to molecular flexibility, hydrophobic interactions, heme Fe coordination and hydrogen bonding.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aromatase Inhibitors / chemistry*
  • Aromatase Inhibitors / pharmacology*
  • Benzodioxoles / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Imidazoles / chemistry*
  • Molecular Structure
  • Quantum Theory

Substances

  • 6-((4-fluorophenyl)(1H-imidazol-1-yl)methyl)-1,3-benzodioxol-5-ol
  • Aromatase Inhibitors
  • Benzodioxoles
  • Imidazoles