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

The title compounds, C17H13FN2O3 and C18H16N2O4, 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 me...

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Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2010-10, Vol.66 (10), p.o499-o502
Main Authors: Andrade, L. C. R., Paixão, J. A., Almeida, M. J. M. de, Neves, M. A. C., Sá e Melo, M. L.
Format: Article
Language:English
Subjects:
Aromatase Inhibitors - chemistry
Aromatase Inhibitors - pharmacology
Benzodioxoles - chemistry
Chemical compounds
Crystal structure
Crystallography
Crystallography, X-Ray
Docking
Flexibility
Hydrogen Bonding
Hydrogen bonds
Imidazoles - chemistry
Inhibitors
Iron
Mathematical analysis
Molecular Structure
Molecules
Quantum mechanics
Quantum Theory
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Summary:The title compounds, C17H13FN2O3 and C18H16N2O4, 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.
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270110034773