Enantioselectivity of some 1-(benzofuran-2-yl)-1-(1-H-imidazol-1-yl) alkanes as inhibitors of P450Arom.
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 (P450Arom) 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.
Khodarahmi
G A
GA
Welsh School of Pharmacy, Cardiff University, Cathays Park, UK.
Smith
H J
HJ
Nicholls
P J
PJ
Ahmadi
M
M
D000473:Alkanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D047072:Aromatase Inhibitors; D001572:Benzofurans / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D007093:Imidazoles / Q000494:pharmacology*; D008861:Microsomes / Q000737:chemistry; D010920:Placenta; D013237:Stereoisomerism
D000473:Alkanes; D047072:Aromatase Inhibitors; D001572:Benzofurans; D004791:Enzyme Inhibitors; D007093:Imidazoles