Document Detail


Synthesis of sphingomyelin carbon analogues as sphingomyelinase inhibitors.
MedLine Citation:
PMID:  12098296     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The highly efficient and stereocontrolled syntheses of sphingomyelin carbon analogues 1 and 2 were achieved by effectively utilizing Hofmann rearrangement of enantiomerically pure beta-hydroxyamide 7, which was prepared by an asymmetric hydrogenation of alpha-acyl-gamma-butyrolactone 9 and ring opening with NH(3). Intermediary isocyanate 6 was selectively trapped with the vicinal hydroxy group in an intramolecular fashion to produce an oxazolidinone derivative, 5. In the synthesis of a quite polar compound such as 1, a convenient one-pot procedure of the introduction of a benzyloxycarbonyl group into the hydroxy group resulting from the oxazolidinone ring opening is another key point, because, in addition to the efficiency, this protecting group was easily removable by a simple procedure and workup at the final step. Both synthesized compounds 1 and 2 showed moderate inhibitory activity toward sphingomyelinase from B. cereus.
Authors:
Toshikazu Hakogi; Yoshiko Monden; Misako Taichi; Seiji Iwama; Shinobu Fujii; Kiyoshi Ikeda; Shigeo Katsumura
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  67     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2002 Jul 
Date Detail:
Created Date:  2002-07-05     Completed Date:  2003-01-16     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4839-46     Citation Subset:  IM    
Affiliation:
School of Science, Kwansei Gakuin University, Gakuen, Sanda, Hyogo 669-1337, Japan.
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MeSH Terms
Descriptor/Qualifier:
Apoptosis
Bacillus cereus / enzymology
Chemistry, Organic / methods
Chromatography, High Pressure Liquid
Cyclization
Dose-Response Relationship, Drug
Enzyme Inhibitors / chemical synthesis*
Indicators and Reagents
Molecular Structure
Spectroscopy, Fourier Transform Infrared
Sphingomyelin Phosphodiesterase / antagonists & inhibitors*,  chemistry
Sphingomyelins / chemical synthesis*,  chemistry,  metabolism
Stereoisomerism
Chemical
Reg. No./Substance:
0/Enzyme Inhibitors; 0/Indicators and Reagents; 0/Sphingomyelins; EC 3.1.4.12/Sphingomyelin Phosphodiesterase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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