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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
16
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pubmed:dateCreated |
2010-6-21
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pubmed:abstractText |
A highly diastereoselective synthesis of 2-amino alcohol derivatives bearing a difluoromethylphosphonothioate group at the 3-position was achieved through LiAlH(O-t-Bu)(3)-mediated reduction of the corresponding alpha-amino ketones. The phosphonothioate moiety of the product was readily converted into the corresponding phosphonate by oxidation with m-CPBA, followed by aqueous workup. The developed methods should be useful for SAR studies of SMA-7, a potent inhibitor of SMases.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Aug
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pubmed:issn |
1520-6904
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pubmed:author |
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pubmed:issnType |
Electronic
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pubmed:day |
21
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pubmed:volume |
74
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
6350-3
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pubmed:meshHeading |
pubmed-meshheading:19610607-Alkanes,
pubmed-meshheading:19610607-Animals,
pubmed-meshheading:19610607-Enzyme Inhibitors,
pubmed-meshheading:19610607-Organophosphorus Compounds,
pubmed-meshheading:19610607-PC12 Cells,
pubmed-meshheading:19610607-Phosphonic Acids,
pubmed-meshheading:19610607-Rats,
pubmed-meshheading:19610607-Sphingomyelin Phosphodiesterase,
pubmed-meshheading:19610607-Sphingomyelins,
pubmed-meshheading:19610607-Stereoisomerism,
pubmed-meshheading:19610607-Structure-Activity Relationship,
pubmed-meshheading:19610607-Substrate Specificity
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pubmed:year |
2009
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pubmed:articleTitle |
Diastereoselective synthesis of gamma-amino-delta-hydroxy-alpha,alpha-difluorophosphonates: a vehicle for structure-activity relationship studies on SMA-7, a potent sphingomyelinase inhibitor.
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pubmed:affiliation |
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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