Solid-phase Synthesis of Highly Diverse Purine-Hydroxyquinolinone Bisheterocycles

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F10%3A10215444" target="_blank" >RIV/61989592:15310/10:10215444 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
Solid-phase Synthesis of Highly Diverse Purine-Hydroxyquinolinone Bisheterocycles
Original language description
Solid-phase synthesis of bisheterocyclic compounds that contain purine and 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 BAL linker. After the arylation of amines with 2,6-dichloropurine via its C6, purine N9 was alkylated and subsequently the chlorine atom at purine C2 was substituted with aliphatic diamines. The resulting terminal aminogroup was used as the starting point for the synthesis of 3-hydroxyquinolin-4(1H)-one precursores based on the acylation with 1-methyl-2-aminoterephtalate 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 cyclisation to the target purine-hydroxyquinolinone bisheterocycles was accomplished by heating in acetic or trifluoroacetic acid.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/ME09057" target="_blank" >ME09057: Research of new organic compounds with anticancer activity with use of combinatorial chemistry</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year
2010
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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