Document Detail


Solid-phase synthesis of highly diverse purine-hydroxyquinolinone bisheterocycles.
MedLine Citation:
PMID:  20849113     Owner:  NLM     Status:  In-Process    
Abstract/OtherAbstract:
Solid-phase synthesis of bisheterocyclic compounds that contain purine and the 3-hydroxyquinolin-4(1H)-one skeleton connected with an aliphatic spacer of a different length/structure is described. The reaction sequence started from the primary amines immobilized on aminomethylated polystyrene resin equipped with an acid-labile linker (4-(4-formyl-3-methoxyphenoxy)butyric acid). After the arylation of amines with 2,6-dichloropurine via its C(6), purine N(9) was alkylated and subsequently the chlorine at purine C(2) was substituted with aliphatic diamines. The resulting terminal amino group was used as the starting point for the synthesis of 3-hydroxyquinolin-4(1H)-one precursors based on the acylation with 3-amino-4-(methoxycarbonyl)benzoic acid followed by the saponification of the methyl ester and esterification of the resulting carboxylic acid with various haloketones. The intermediates were cleaved from the resin, and their cyclization to the target purine-hydroxyquinolinone bisheterocycles was accomplished by heating in acetic or trifluoroacetic acid.
Authors:
Barbora Vanková; Jan Hlavác; Miroslav Soural
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-09-17
Journal Detail:
Title:  Journal of combinatorial chemistry     Volume:  12     ISSN:  1520-4774     ISO Abbreviation:  J Comb Chem     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-11-08     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100886263     Medline TA:  J Comb Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  890-4     Citation Subset:  IM    
Affiliation:
Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, University of Palacký, 771 46 Olomouc, Czech Republic.
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