Expedient and Practical Synthesis of CERT-Dependent Ceramide Trafficking Inhibitor HPA-12 and Its Analogues

The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-depen...

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Bibliographic Details
Published in:Organic letters 2011-04, Vol.13 (7), p.1642-1645
Main Authors: Ďuriš, Andrej, Wiesenganger, Tomáš, Moravčíková, Daniela, Baran, Peter, Kožíšek, Jozef, Daïch, Adam, Berkeš, Dušan
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Amides - pharmacology
Catalysis
Ceramides - metabolism
Chemical Sciences
Medicinal Chemistry
Models, Molecular
Molecular Structure
Organic chemistry
Protein-Serine-Threonine Kinases - antagonists & inhibitors
Protein-Serine-Threonine Kinases - metabolism
Stereoisomerism
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Summary:The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol2001057