Literature DB >> 16671809

Chemical transformation of prostaglandin-A2: a novel series of C-10 halogenated, C-12 hydroxylated prostaglandin-A2 analogues.

Anokha S Ratnayake1, Tim S Bugni, Charles A Veltri, Jack J Skalicky, Chris M Ireland.   

Abstract

[reaction: see text] Synthesis of a novel class of C-10 halogenated and C-12 oxygenated prostaglandin-A(2) derivatives (6a-6c) has been accomplished. (15S)-Prostaglandin-A(2) (1), from the gorgonian Plexaura homomalla, served as the starting material for the synthesis. The absolute configuration was determined using NMR.

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Year:  2006        PMID： 16671809      PMCID： PMC2533845          DOI： 10.1021/ol0606583

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Isolation and chemical conversions of prostaglandins from Plexaura homomalla: Preparation of prostaglandin E2, prostaglandin F2alpha, and their 5,6-trans isomers.

Authors:  W P Schneider; G L Bundy; F H Lincoln; E G Daniels; J E Pike
Journal:  J Am Chem Soc       Date:  1977-02-16       Impact factor: 15.419

2.  Occurrence of esters of (15S)-prostaglandin A 2 and E 2 in coral.

Authors:  W P Schneider; R D Hamilton; L E Rhuland
Journal:  J Am Chem Soc       Date:  1972-03-22       Impact factor: 15.419

3.  Cyclopentenone prostaglandins of the J series inhibit the ubiquitin isopeptidase activity of the proteasome pathway.

Authors:  J E Mullally; P J Moos; K Edes; F A Fitzpatrick
Journal:  J Biol Chem       Date:  2001-06-04       Impact factor: 5.157

4.  Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

Authors:  Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

5.  The occurrence of two new prostaglandin derivatives (15-epi-PGA2 and its acetate, methyl ester) in the gorgonian Plexaura homomalla chemistry of coelenterates. XV.

Authors:  A J Weinheimer; R L Spraggins
Journal:  Tetrahedron Lett       Date:  1969-12       Impact factor: 2.415

6.  Pharmacophore model for novel inhibitors of ubiquitin isopeptidases that induce p53-independent cell death.

Authors:  J E Mullally; F A Fitzpatrick
Journal:  Mol Pharmacol       Date:  2002-08       Impact factor: 4.436

7.  Punaglandins, chlorinated prostaglandins, function as potent Michael receptors to inhibit ubiquitin isopeptidase activity.

Authors:  Sheryl M Verbitski; James E Mullally; Frank A Fitzpatrick; Chris M Ireland
Journal:  J Med Chem       Date:  2004-04-08       Impact factor: 7.446

8.  Synthesis of C(10)-halogenated prostaglandins.

Authors:  J N Dominguez; A Taddei; M Cordero; I Blanca
Journal:  J Pharm Sci       Date:  1994-04       Impact factor: 3.534
  8 in total
  1 in total

1.  Distinct pathways generate peptides from defective ribosomal products for CD8+ T cell immunosurveillance.

Authors:  Brian P Dolan; Lily Li; Charles A Veltri; Chris M Ireland; Jack R Bennink; Jonathan W Yewdell
Journal:  J Immunol       Date:  2011-01-12       Impact factor: 5.422
  1 in total

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