Abstract:
:The synthesis and gastric antisecretory activities of the delta 4,5-cis, delta 4,5-trans, and 4,5-acetylenic analogues of 15-deoxy-16-hydroxy-16-methyl prostaglandin E1 methyl ester are described. The key step in the preparation of these compounds involved the stereospecific conjugate addition of a cuprate reagent to the appropriate cyclopentenones. Although the trans and acetylenic derivatives were weak inhibitors of gastric acid secretion, the cis olefin was more potent and longer acting than the saturated parent compound. Selectivity with respect to unwanted diarrheagenic effects was found to be improved over that of both the parent 16-hydroxy compound and the reference standards, (15S)-15-methyl- and 16,16-dimethylprostaglandin E2.
journal_name
J Med Chemjournal_title
Journal of medicinal chemistryauthors
Collins PW,Dajani EZ,Pappo R,Gasiecki AF,Bianchi RG,Woods EMdoi
10.1021/jm00360a002subject
Has Abstractpub_date
1983-06-01 00:00:00pages
786-90issue
6eissn
0022-2623issn
1520-4804journal_volume
26pub_type
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