Prostaglandin prodrugs. II: New method for synthesizing prostaglandin C1-aliphatic esters.
A new method for synthesizing C1-aliphatic esters of dinoprost and dinoprostone without using hydroxyl protective groups is described. Reaction of the prostaglandin with an alkyl halide in the presence of the sterically hindered amine N,N-diisopropylethylamine proceeds smoothly to give C1-esters in various solvents at ambient or slightly elevated temperatures. Polar solvents were strongly catalytic, and even the hindered tert-butyl esters were synthesized by employing solvents such as dimethylformamide or dimethyl sulfoxide. Biological evaluation in the hamster antifertility assay showed that some esters maintained high bioactivity.
D000818:Animals; D003271:Contraceptive Agents, Female; D006224:Cricetinae; D005260:Female; D008722:Methods; D011465:Prostaglandins, Synthetic / Q000138:chemical synthesis* / Q000494:pharmacology
D003271:Contraceptive Agents, Female; D011465:Prostaglandins, Synthetic