BIOMAT Database Logo BIOMAT Database Logo

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. 2010

L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
CEMDRX, Departamento de Física, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, P-3004-516 Coimbra, Portugal.

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.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D011789 Quantum Theory The theory that the radiation and absorption of energy take place in definite quantities called quanta (E) which vary in size and are defined by the equation E Quantum Theories,Theories, Quantum,Theory, Quantum
D006860 Hydrogen Bonding A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds. Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D047072 Aromatase Inhibitors Compounds that inhibit AROMATASE in order to reduce production of estrogenic steroid hormones. Aromatase Inhibitor,Inhibitor, Aromatase,Inhibitors, Aromatase
D052117 Benzodioxoles Compounds based on benzene fused to oxole. They can be formed from methylated CATECHOLS such as EUGENOL. Methylenedioxybenzenes,1,3-Dioxaindans,1,3-Dioxindans,1,3 Dioxaindans,1,3 Dioxindans
D018360 Crystallography, X-Ray The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies

Related Publications

L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
4-(2H-1,3-Benzodioxol-5-yl)-1-(4-methyl-phenyl)-1H-pyrazol-5-amine.
May 2013, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate.
January 2012, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
A monoclinic polymorph of 4-(2H-1,3-benzodioxol-5-yl)-1-(4-methyl-phen-yl)-1H-pyrazol-5-amine.
October 2015, Acta crystallographica. Section E, Crystallographic communications,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
1-[5-(2H-1,3-Benzodioxol-5-yl)-3-(4-methyl-phen-yl)-2-pyrazolin-1-yl]ethanone.
May 2013, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
N-[(E)-1,3-Benzodioxol-5-yl-methyl-idene]-4-methyl-aniline.
November 2010, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
1-[(1-Methyl-1H-imidazol-5-yl)meth-yl]-1H-indole-5-carbonitrile.
December 2012, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
2-[(6-Nitro-1,3-benzodioxol-5-yl)methyl-idene]malononitrile.
December 2011, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
2-[5-(1,3-Benzodioxol-5-yl)-3-ferrocenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia-zole.
September 2010, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
4-Meth-oxy-5-[4-(4-meth-oxy-1,3-benzodioxol-5-yl)perhydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole.
June 2008, Acta crystallographica. Section E, Structure reports online,
L C R Andrade, and J A Paixão, and M J M deAlmeida, and M A C Neves, and M L Sá e Melo
2-(1,3-Benzodioxol-5-yl)-1H-benzimid-azole.
February 2014, Acta crystallographica. Section E, Structure reports online,
Copied contents to your clipboard!