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Aminoacetyl moiety as a potential surrogate for diacylhydrazine group of SC-51089, a potent PGE2 antagonist, and its analogs.
- Source :
-
Journal of medicinal chemistry [J Med Chem] 1996 Jan 19; Vol. 39 (2), pp. 609-13. - Publication Year :
- 1996
-
Abstract
- 8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (1, SC-51089) is a functional PGE2 antagonist selective for the EP1 receptor subtype with antinociceptive activity. During metabolism in cultured rat hepatocytes, SC-51089, which contains a diacylhydrazine moiety, has been shown to release hydrazine. Analogs of SC-51089, in which the diacylhydrazine functionality has been replaced by isosteric and isoelectronic groups, have been synthesized and have been shown to be analgesics and PGE2 antagonists of the EP1 subtype. This report discusses the structure-activity relationships within these series.
- Subjects :
- Analgesics chemistry
Animals
Cells, Cultured
Guinea Pigs
Ileum drug effects
Ileum metabolism
In Vitro Techniques
Liver cytology
Liver drug effects
Magnetic Resonance Spectroscopy
Oxazepines chemistry
Prostaglandin Antagonists chemistry
Rats
Analgesics pharmacology
Dinoprostone antagonists & inhibitors
Hydrazines chemistry
Hydrazines pharmacology
Oxazepines pharmacology
Prostaglandin Antagonists pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 0022-2623
- Volume :
- 39
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 8558534
- Full Text :
- https://doi.org/10.1021/jm950454k