Efficient Solid-Phase Synthesis of 2-Substituted-3-Hydroxy-4(1H)-Quinolinone-7-Carboxamides withTwo Diversity Positions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F07%3A00004869" target="_blank" >RIV/61989592:15310/07:00004869 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
Efficient Solid-Phase Synthesis of 2-Substituted-3-Hydroxy-4(1H)-Quinolinone-7-Carboxamides withTwo Diversity Positions
Original language description
A highly efficient solid-phase synthesis of 2-substituted-3-hydroxy-4(1H)-quinolinone-7-carboxamides was developed using anthranilates and bromoketones as the key synthons. Primary amines immobilized to an acid-cleavable BAL linker were acylated with 1-methyl-2-aminoterephtalate. After cleavage of the methyl ester, bromoketones were used to form resin-bound phenacyl esters. Acid-mediated cleavage and subsequent cyclization in solution afforded 3-hydroxy-4(1H)-quinolinones in high purity and yield. Highly efficient solid-phase synthesis (purity > 90%, yield > 80%, synthetic time ) 2 days using commercially available synthons) is amenable to high-throughput/combinatorial synthesis to match the high-throughput screening capability.
Czech name
Efektivní syntéza 2-substituovaných-3-hydroxy-4(1H)-chinolon-7-karboxamidů
Czech description
Práce popisuje efektivní způsob syntézy 2-substituovaných-3-hydroxy-4(1H)-chinolonů-7-carboxamidů na pevné fázi. Výchozí aminy byly imobilizovány na kysele štěpitelný BAL linker, acylovány 1-methyl-2-aminotereftalovou kyselinou. Po odštěpení methylesterové skupiny byly připraveny fenacylestery, které byly dále cyklizovány za vzniku příslušných chinolonů za současného odštěpení z matrice.
Classification
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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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2007
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Combinatorial Chemistry
ISSN
1520-4766
e-ISSN
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Volume of the periodical
9
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
4
Pages from-to
793-796
UT code for WoS article
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EID of the result in the Scopus database
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