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. 2013 Mar 13;18(3):3227-40.
doi: 10.3390/molecules18033227.

Synthesis and antimicrobial activity of novel substituted ethyl 2-(quinolin-4-yl)-propanoates

M Akram Khan  1 , Keith Miller, Kim Drummond Rainsford, Yong Zhou
Affiliations

Synthesis and antimicrobial activity of novel substituted ethyl 2-(quinolin-4-yl)-propanoates

M Akram Khan et al. Molecules. .

Abstract

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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Figures

Scheme 1
Scheme 1
Synthesis of 4-chloroquinolines and ethyl 2-(quinolin-4-yl)propanoates.
Scheme 2
Scheme 2
Mechanism of the de-ethoxycarbonylation by the Krapcho reaction.
Scheme 3
Scheme 3
Formation of side products 13 and 14 during the synthesis of 10k and 10m.
Figure 1
Figure 1
Inhibitory effects of compounds 10a–h on H. pylori 3339 after 7 days.
Figure 2
Figure 2
Inhibitory effects of compounds 10i–p, 13 and 14 on H. pylori 3339 after 7 days.
Figure 3
Figure 3
Inhibitory effects of compounds 10a–h on H. pylori 26695 after 7 days.
Figure 4
Figure 4
Inhibitory effects of compounds 10i–p, 13 and 14 on H. pylori 26695 after 7 days.
See this image and copyright information in PMC

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