Synthesis and evaluation of the antiovulatory activity of a variety of melatonin analogues.
A series of melatonin analogues was synthesized and examined for ovulation-blocking activity. Deviation from the 5-methoxy group or substitution of the 1 position prevented activity. Activity was not particularly sensitive to minor variations in the N-acyl group nor was it significantly altered by methylation of position 2 or the alpha-methylene; however, a pronounced enhancement resulted from halogenation of the 6 position.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D008550:Melatonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D010060:Ovulation / Q000187:drug effects*; D051381:Rats; D012701:Serotonin; D013329:Structure-Activity Relationship
D012701:Serotonin; D008550:Melatonin