title: 6beta-Methyl-B-norandrostenedione.
abstract: The title compound, C(19)H(26)O(2), a B-norandrogen with a 6beta-methyl group, is a recently identified and experimentally tested potent new aromatase inhibitor. It shares structural and physicochemical similarities both with the natural substrate of the enzyme, androstenedione, and with exemestane, another potent aromatase inhibitor having a 6-methylidene group. X-ray diffraction results indicate that the B-nor molecule and exemestane have nearly the same oxygen-oxygen and methyl-methyl separations, though they have distinct configurations of the hydrophobic groups at the 6-position. These structural comparisons allow correlations to be inferred between the active site geometry of the molecules and the aromatase inhibition power of the studied compound.
authors.affiliation: CEMDRX, Departamento de Física, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, P-3004-516 Coimbra, Portugal. lourdes@pollux.fis.uc.pt
authors.forename: L C R
authors.initials: LC
authors.lastname: Andrade
authors.forename: M J M
authors.initials: MJ
authors.lastname: de Almeida
authors.forename: M A C
authors.initials: MA
authors.lastname: Neves
authors.forename: T C P
authors.initials: TC
authors.lastname: Dinis
authors.forename: M L
authors.initials: ML
authors.lastname: Sá e Melo
mesh_terms: D000730:Androstadienes / Q000737:chemistry*; D000735:Androstenedione / Q000737:chemistry* / Q000494:pharmacology; D047072:Aromatase Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D001665:Binding Sites; D002384:Catalysis; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D009654:Norsteroids / Q000737:chemistry*; D011485:Protein Binding; D014961:X-Ray Diffraction
chemical_list: C549893:6-methyl-B-norandrostenedione; D000730:Androstadienes; D047072:Aromatase Inhibitors; D009654:Norsteroids; D000735:Androstenedione