Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates

Substituted 4-hydroxyquinolines were synthesized from anilines and diethyl 2-(ethoxymethylene)malonate by the Gould-Jacobs reaction via cyclization of the intermediate anilinomethylenemalonate followed by hydrolysis and decarboxylation. The 4-hydroxyquinolines reacted with phosphorous oxychloride to...

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Detalles Bibliográficos
Autores principales: Khan, M. Akram, Miller, Keith, Rainsford, Kim Drummond, Zhou, Yong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270033/
https://www.ncbi.nlm.nih.gov/pubmed/23486102
http://dx.doi.org/10.3390/molecules18033227
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author Khan, M. Akram
Miller, Keith
Rainsford, Kim Drummond
Zhou, Yong
author_facet Khan, M. Akram
Miller, Keith
Rainsford, Kim Drummond
Zhou, Yong
author_sort Khan, M. Akram
collection PubMed
description Substituted 4-hydroxyquinolines were synthesized from anilines and diethyl 2-(ethoxymethylene)malonate by the Gould-Jacobs reaction via cyclization of the intermediate anilinomethylenemalonate followed by hydrolysis and decarboxylation. The 4-hydroxyquinolines reacted with phosphorous oxychloride to form 4-chloroquinolines, which reacted on heating with diethyl sodiomethylmalonate in DMF to yield moderate yields of substituted ethyl 2-(quinolin-4-yl)propanoates, many of which showed potent antimicrobial activity against Helicobacter pylori.
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spelling pubmed-62700332018-12-20 Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates Khan, M. Akram Miller, Keith Rainsford, Kim Drummond Zhou, Yong Molecules Article Substituted 4-hydroxyquinolines were synthesized from anilines and diethyl 2-(ethoxymethylene)malonate by the Gould-Jacobs reaction via cyclization of the intermediate anilinomethylenemalonate followed by hydrolysis and decarboxylation. The 4-hydroxyquinolines reacted with phosphorous oxychloride to form 4-chloroquinolines, which reacted on heating with diethyl sodiomethylmalonate in DMF to yield moderate yields of substituted ethyl 2-(quinolin-4-yl)propanoates, many of which showed potent antimicrobial activity against Helicobacter pylori. MDPI 2013-03-13 /pmc/articles/PMC6270033/ /pubmed/23486102 http://dx.doi.org/10.3390/molecules18033227 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Khan, M. Akram
Miller, Keith
Rainsford, Kim Drummond
Zhou, Yong
Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates
title Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates
title_full Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates
title_fullStr Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates
title_full_unstemmed Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates
title_short Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl)-propanoates
title_sort synthesis and antimicrobial activity of novel substituted ethyl 2-(quinolin-4-yl)-propanoates
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270033/
https://www.ncbi.nlm.nih.gov/pubmed/23486102
http://dx.doi.org/10.3390/molecules18033227
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