Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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

Similar articles

See all similar articles

Cited by

References

    1. Williamson W.R.N., editor. Anti-Inflammatory Compounds. Marcel Dekker; New York, NY, USA: 1987. p. 250.
    1. Lavrado J., Moreira R., Paulo A. Indoloquinolines as scaffolds for drug discovery. Curr. Med. Chem. 2010;17:2348–2370. doi: 10.2174/092986710791698521. - DOI - PubMed
    1. Price C.C., Boekelheide V. A synthesis of substituted 4-aminoquinolines. J. Am. Chem. Soc. 1946;68:1246–1250. doi: 10.1021/ja01211a031. - DOI - PubMed
    1. Elderfield R.C., Gensler W.J., Birstein O., Kreysa F.J., Maynard J.T., Galbreath J. Synthesis of certain simple 4-aminoquinoline derivatives. J. Am. Chem. Soc. 1946;68:1250–1251. doi: 10.1021/ja01211a032. - DOI - PubMed
    1. Draker N.L., Creech H.J., Draper D., Garman J.A., Haywood S., Peck R.M., Walton E, van Hook J.O. Synthetic antimalarials. The preparation and properties of 7-chloro-4-(4-diethyamino-1-methylbutylamino)-quinoline. J. Am. Chem. Soc. 1946;68:1214–1240. doi: 10.1021/ja01211a022. - DOI - PubMed

Publication types

MeSH terms

LinkOut - more resources