Solid-phase Synthesis of Highly Diverse Purine-Hydroxyquinolinone Bisheterocycles

Kód výsledku v 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>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Solid-phase Synthesis of Highly Diverse Purine-Hydroxyquinolinone Bisheterocycles

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Solid-phase Synthesis of Highly Diverse Purine-Hydroxyquinolinone Bisheterocycles

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/ME09057" target="_blank" >ME09057: Výzkum nových sloučenin s protinádorovou aktivitou za pomoci kombinatoriální chemie</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2010

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Combinatorial Chemistry

ISSN

1520-4766

e-ISSN

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Svazek periodika

12

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

5

Strana od-do

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Kód UT WoS článku

000283810600014

EID výsledku v databázi Scopus

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