Enantioselectivity of some 1-(benzofuran-2-yl)-1-(1-H-imidazol-1-yl) alkanes as inhibitors of P450(Arom)

Article abstract of DOI:10.1111/j.2042-7158.1998.tb03352.x

The low stereospecificity of the enantiomers of 1-[(benzofuran-2-yl)-4-chlorophenylmethyl]imidazole (6, R = H, R' = 4'-Cl) and the corresponding 4-fluoro compound as inhibitors of aromatase (P450(Arom)) has been explored using 1-(5,7-dichlorobenzofuran-2-yl)-1-(1H-imidaz-1-yl)ethane (7, R₁ = R₂ = Cl, R = CH₃), -propane (7, R₁ = R₂ = Cl, R = C₂H₅), and the corresponding 5,7-dibromo compounds resolved as their dibenzoyl-D (or -L) tartrates. Low enantioselectivity ratios of 4.8 (5,7-diCl) and 12.6 (5,7-diBr) were shown for the ethanes. The values for the corresponding propanes were 8.3 and 5.2, respectively, and for these compounds the stereoselectivity was reversed.