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Titolo:
Synthesis of the first selective irreversible inhibitor of neutral sphingomyelinase
Autore:
Arenz, C; Giannis, A;
Indirizzi:
Univ Karlsruhe, Inst Organ Chem, D-76128 Karlsruhe, Germany Univ Karlsruhe Karlsruhe Germany D-76128 hem, D-76128 Karlsruhe, Germany
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 1, , anno: 2001,
pagine: 137 - 140
SICI:
1434-193X(200101):1<137:SOTFSI>2.0.ZU;2-Y
Fonte:
ISI
Lingua:
ENG
Soggetto:
NECROSIS-FACTOR-ALPHA; TRICHOPEZIZA-MOLLISSIMA; CELL-DIFFERENTIATION; SCYPHOSTATIN; CERAMIDE; IDENTIFICATION; AEROPLYSININ; GLUTATHIONE; DISCOMYCETE; APOPTOSIS;
Keywords:
lipids; natural products; enzyme inhibitors; total synthesis; ceramide;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
27
Recensione:
Indirizzi per estratti:
Indirizzo: Giannis, A Univ Karlsruhe, Inst Organ Chem, Richard Willstatter Allee 2, D-76128 Karlsruhe, Germany Univ Karlsruhe Richard Willstatter Allee 2 Karlsruhe Germany D-76128
Citazione:
C. Arenz e A. Giannis, "Synthesis of the first selective irreversible inhibitor of neutral sphingomyelinase", EUR J ORG C, (1), 2001, pp. 137-140

Abstract

The sphingolipid ceramide is a candidate second messenger assumed to be involved in fundamental processes such as growth control, inflammation and apoptosis. Many aspects of ceramide-mediated processes remain to be clarified, including the question of which of the different sphingomyelinases is critical for the stimulus-induced ceramide production. Selective inhibitors ofthe sphingomyelinases are useful tools for clarifying the biological role of these enzymes and, moreover, appear to be interesting motives for the development of pharmacological agents for an experimental therapy of inflammatory diseases. The full synthesis of N-[2-hydroxy-1-(8-oxo-1-oxa-spiro[2.5]octa-4,6-diene-5-ylcarbamoyl)-ethyl] decanamide (2), the first selective irreversible inhibitor of neutral sphingomyelinase, is described and the relevant analytical data are given. The inhibitor 2 was obtained by a five-stepsynthesis starting from D-serine.

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Documento generato il 03/04/20 alle ore 07:29:37