Literature DB >> 8558534

Aminoacetyl moiety as a potential surrogate for diacylhydrazine group of SC-51089, a potent PGE2 antagonist, and its analogs.

E A Hallinan1, T J Hagen, S Tsymbalov, R K Husa, A C Lee, A Stapelfeld, M A Savage.   

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 Analogs of SC-51089, in which the diacylhydrazine functionality has been replaced by isosteric and isoelectronic groups, have been synthesized and have been shown to be analgesics and PGE2 antagonists of the EP1 subtype.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.

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Year:  1996        PMID： 8558534     DOI： 10.1021/jm950454k

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  9 in total

1.  One-pot tandem Ugi-4CR/S(N)Ar approach to highly functionalized quino[2,3-b][1,5]benzoxazepines.

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Journal:  Mol Divers       Date:  2015-12-24       Impact factor: 2.943

2.  Characterization of prostanoid receptors mediating actions of the isoprostanes, 8-iso-PGE(2) and 8-iso-PGF(2alpha), in some isolated smooth muscle preparations.

Authors:  W Sametz; S Hennerbichler; S Glaser; R Wintersteiger; H Juan
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3.  EP2 Receptor Signaling Regulates Microglia Death.

Authors:  Yujiao Fu; Myung-Soon Yang; Jianxiong Jiang; Thota Ganesh; Eunhye Joe; Raymond Dingledine
Journal:  Mol Pharmacol       Date:  2015-02-25       Impact factor: 4.436

4.  Involvement of EP1 and EP2 receptors in the regulation of the Na,K-ATPase by prostaglandins in MDCK cells.

Authors:  Keikantse Matlhagela; Mary Taub
Journal:  Prostaglandins Other Lipid Mediat       Date:  2006-01-27       Impact factor: 3.072

5.  The neuroprotective effect of prostaglandin E2 EP1 receptor inhibition has a wide therapeutic window, is sustained in time and is not sexually dimorphic.

Authors:  Takato Abe; Alexander Kunz; Munehisa Shimamura; Ping Zhou; Josef Anrather; Costantino Iadecola
Journal:  J Cereb Blood Flow Metab       Date:  2008-07-23       Impact factor: 6.200

6.  Michael Reaction of 3-aAryl-2,4-Dicarboethoxy-5-Hydroxy-5-Methylcyclohexanones.

Authors:  Fawzia Zakaria El-Ablack; M A Metwally; A M Khalil
Journal:  Org Chem Int       Date:  2015-09-01

7.  N-Cyclo-hexyl-5H,7H-13,15-dimethyl-9-nitro-5-oxophenanthrido[4,4a,5-bc][1,4]benzoxazepine-7-carboxamide.

Authors:  Jia-Lu Luo; Jin-Long Wu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-25

8.  Microglial inhibition of neuroprotection by antagonists of the EP1 prostaglandin E2 receptor.

Authors:  Noel G Carlson; Monica A Rojas; John-David Black; Jonathan W Redd; John Hille; Kenneth E Hill; John W Rose
Journal:  J Neuroinflammation       Date:  2009-02-17       Impact factor: 8.322

9.  Aspirin prevents colorectal cancer metastasis in mice by splitting the crosstalk between platelets and tumor cells.

Authors:  Paloma Guillem-Llobat; Melania Dovizio; Annalisa Bruno; Emanuela Ricciotti; Valerio Cufino; Angela Sacco; Rosalia Grande; Sara Alberti; Vincenzo Arena; Mariangela Cirillo; Carlo Patrono; Garret A FitzGerald; Dieter Steinhilber; Alessandro Sgambato; Paola Patrignani
Journal:  Oncotarget       Date:  2016-05-31
  9 in total

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