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  • Title: Synthesis and gastrointestinal pharmacology of a 3E,5Z diene analogue of misoprostol.
    Author: Collins PW, Kramer SW, Gasiecki AF, Weier RM, Jones PH, Gullikson GW, Bianchi RG, Bauer RF.
    Journal: J Med Chem; 1987 Jan; 30(1):193-7. PubMed ID: 3100798.
    Abstract:
    A stereospecific synthesis and the gastric antisecretory and diarrheal activity of a 3E,5Z diene analogue of misoprostol are described. The key intermediate in the synthesis was an alpha chain truncated acetylene that was obtained by a cuprate/enolate capture procedure on the corresponding cyclopentenone. Palladium-catalyzed coupling of the acetylene with methyl 4-iodo-3(E)-butenoate provided the conjugated enyne. Although selective hydrogenation of the enyne with Lindlar catalyst failed, the desired 3E,5Z diene was obtained with P-2 nickel as catalyst. The diene was about 3 times more potent than misoprostol in inhibiting gastric acid secretion in dogs and also in producing diarrhea in rats.
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