Dehydrative metabolites of 1-(3-chlorophenyl)-1methyl-2-phenyl-2-(2-pyridine)ethanol as potential hypocholesteremic agents.
The E and Z isomers of 2-[2-(3-chlorophenyl)-1-phenyl-1-propenyl]pyridine (2a,b) and 2-[2-(3-chlorophenyl)-1-(4-hydroxyphenyl)-1-propenyl]pyridine (4a,b) were synthesized and separated as possible metabolites of 1-(3-chlorophenyl)-1-methyl-2-phenyl-2-(2-pyridine)ethanol (1a). Following administration of 1a to rats, a HPLC system was used to examine urine and serum specimens for the less polar metabolites of 1a. Isomers 2a and 2b were not detected but their hydroxylated derivatives 4a and 4b were observed as minor metabolites. Compounds 2a,b and 4a,b exhibited hypocholesteremic activity in rats; compounds 4a and 4b are of special interest because they possessed relatively low estrogenicity.
D000818:Animals; D000924:Anticholesteremic Agents / Q000138:chemical synthesis* / Q000378:metabolism; D002369:Castration; D002851:Chromatography, High Pressure Liquid; D045166:Estradiol Congeners / Q000138:chemical synthesis; D005260:Female; D008297:Male; D011725:Pyridines / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism
D000924:Anticholesteremic Agents; D045166:Estradiol Congeners; D011725:Pyridines; C015749:1-(3-chlorophenyl)-1-methyl-2-phenyl-2-(2-pyridine)ethanol