Collins P W, Kramer S W, Gullikson G W
Gastrointestinal Diseases Research Department, G.D. Searle & Co., Skokie, Illinois 60077.
J Med Chem. 1987 Nov;30(11):1952-5. doi: 10.1021/jm00394a004.
A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization reaction to provide the necessary hydroxycyclopentenone, and a two-carbon-homologation procedure. The fluoro analogue was much less potent as a gastric antisecretory and mucosal protective agent than enisoprost.
制备了依尼前列素的4-氟类似物，并在动物中评估其胃抗分泌和粘膜保护活性。合成以铜酸盐化学为核心，但也涉及维蒂希反应以生成顺式氟代烯基部分、呋喃重排/异构化反应以提供所需的羟基环戊烯酮，以及双碳同系化过程。该氟类似物作为胃抗分泌和粘膜保护剂的效力远低于依尼前列素。
