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

The low stereospecificity of the enantiomers of 1-[(benzofuran-2-yl)-4-chlo rophenylmethyl]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, R-1 = R-2 = CI, R = CH3), -propane (7, R-1 = R-2 = 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 sh own for the ethanes. The values for the corresponding propanes were 8.3 and 5.2, respectively, and for these compounds the stereoselectivity was rever sed.