Document Detail

Synthesis and absolute stereochemistry of 5-alkyl-5-(3'-hydroxy-1'-methylbutyl)barbituric acid and 5-alkyl-5-(3'-hydroxy-1'-methylbutyl)-2-thiobarbituric acids.
MedLine Citation:
PMID:  1109573     Owner:  NLM     Status:  MEDLINE    
5-Alkyl-5-(3-hydroxy-1-methylbutyl) barbituric acid (2) and 5-alkyl-5-(3-hydroxy-1-methylbutyl)-2-thiobarbituric acids (3) are matabolites of 5-alkyl-5-(2-pentyl) barbituric acid and 5-alkyl-5-(2-pantyl)-2-thiobarbituric acid, respectively. We have synthesized the four possible optical isomers of 2 and 3 by a procedure which established the absolute stereochemistry of each isomer. The two racemic pairs in each case were also prepared. The properties of these synthetic samples of 2 and 3 of known stereochemistry are compared to the properties of 2 and 3 which have been isolated from metabolism studies.
F I Carroll; G N Mitchell
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  18     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1975 Jan 
Date Detail:
Created Date:  1975-03-18     Completed Date:  1975-03-18     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  37-41     Citation Subset:  IM    
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MeSH Terms
Barbiturates / chemical synthesis*
Molecular Conformation
Optical Rotation
Thiones / chemical synthesis
Reg. No./Substance:
0/Barbiturates; 0/Thiones

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