81834-82-4Relevant academic research and scientific papers
Synthesis and Gastrointestinal Pharmacology of a 3E,5Z Diene Analogue of Misoprostol
Collins, Paul W.,Kramer, Steven W.,Gasiecki, Alan F.,Weier, Richard M.,Jones, Peter H.,et al.
, p. 193 - 197 (2007/10/02)
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 α 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 selected hydrogenation of the enyne with Lindlar catalyst failed, the desired 3E,5Z diene was obtained with P-2 nickel as a 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.
Synthesis and Gastric Antisecretory Properties of α Chain Diene Derivatives of Misoprostol
Collins, Paul W.,Gasiecki, Alan F.,Jones, Peter H.,Bauer, Raymond F.,Gullikson, Gary W.,et al.
, p. 1195 - 1201 (2007/10/02)
The synthesis and gastric antisecretory activity in dogs of seven α chain diene derivatives of misoprostol are described.The key intermediates in the preparation of these compounds were C-9 tert-butyldimethylsilyl enol ethers that were obtained by in situ
