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

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2013 Mar 15

PMID 23486102

Citations 1

Authors

M Akram Khan

Keith Miller

Kim Drummond Rainsford

Yong Zhou

Affiliations

Soon will be listed here.

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.

Citing Articles

Palladium-Catalyzed Dehydrogenative Coupling: An Efficient Synthetic Strategy for the Construction of the Quinoline Core.

Carral-Menoyo A, Ortiz-de-Elguea V, Martinez-Nunes M, Sotomayor N, Lete E Mar Drugs. 2017; 15(9).

PMID: 28867803 PMC: 5618415. DOI: 10.3390/md15090276.

References

Warren J . Helicobacter: the ease and difficulty of a new discovery (Nobel lecture). ChemMedChem. 2006; 1(7):672-85. DOI: 10.1002/cmdc.200600121. View

ONeill A, Miller K, Oliva B, Chopra I . Comparison of assays for detection of agents causing membrane damage in Staphylococcus aureus. J Antimicrob Chemother. 2004; 54(6):1127-9. DOI: 10.1093/jac/dkh476. View

Marshall B, Warren J . Unidentified curved bacilli in the stomach of patients with gastritis and peptic ulceration. Lancet. 1984; 1(8390):1311-5. DOI: 10.1016/s0140-6736(84)91816-6. View

Ribeiro M, Vitiello L, Miranda M, Benvengo Y, Godoy A, Mendonca S . Mutations in the 23S rRNA gene are associated with clarithromycin resistance in Helicobacter pylori isolates in Brazil. Ann Clin Microbiol Antimicrob. 2003; 2:11. PMC: 305369. DOI: 10.1186/1476-0711-2-11. View

FUSON R, PARHAM W, Reed L . The synthesis of 7-chloro-4-(l-ethyl-4-piperidylamino)-quinoline (SN-13,425). J Am Chem Soc. 2010; 68:1239. DOI: 10.1021/ja01211a028. View

Lavrado J, Moreira R, Paulo A . Indoloquinolines as scaffolds for drug discovery. Curr Med Chem. 2010; 17(22):2348-70. DOI: 10.2174/092986710791698521. View

Warren J . Gastric pathology associated with Helicobacter pylori. Gastroenterol Clin North Am. 2000; 29(3):705-51. DOI: 10.1016/s0889-8553(05)70139-4. View

Brzozowski T, Konturek P, Sliwowski Z, Kwiecien S, Drozdowicz D, Pawlik M . Interaction of nonsteroidal anti-inflammatory drugs (NSAID) with Helicobacter pylori in the stomach of humans and experimental animals. J Physiol Pharmacol. 2006; 57 Suppl 3:67-79. View

Price C, Roberts R . The synthesis of 4-hydroxyquinolines; through ethoxymethylene malonic ester. J Am Chem Soc. 2010; 68:1204-8. DOI: 10.1021/ja01211a020. View

10.

Bazzoli F, De Luca L, Graham D . Helicobacter pylori infection and the use of NSAIDs. Best Pract Res Clin Gastroenterol. 2001; 15(5):775-85. DOI: 10.1053/bega.2001.0234. View

11.

Hobbs J, Miller K, ONeill A, Chopra I . Consequences of daptomycin-mediated membrane damage in Staphylococcus aureus. J Antimicrob Chemother. 2008; 62(5):1003-8. DOI: 10.1093/jac/dkn321. View

12.

Zhou Y, Taylor B, Smith T, Liu Z, Clench M, Davies N . A novel compound from celery seed with a bactericidal effect against Helicobacter pylori. J Pharm Pharmacol. 2009; 61(8):1067-77. DOI: 10.1211/jpp/61.08.0011. View

13.

Hilliard J, Goldschmidt R, Licata L, Baum E, Bush K . Multiple mechanisms of action for inhibitors of histidine protein kinases from bacterial two-component systems. Antimicrob Agents Chemother. 1999; 43(7):1693-9. PMC: 89345. DOI: 10.1128/AAC.43.7.1693. View

14.

Chopra I . The 2012 Garrod lecture: discovery of antibacterial drugs in the 21st century. J Antimicrob Chemother. 2012; 68(3):496-505. DOI: 10.1093/jac/dks436. View

15.

Wu C, Wu M, Chen C, Li M, Lin J, Chen G . The interaction of H. pylori infection and NSAIDs in cyclooxygenase-2 mRNA expression in gastric antral, corpus mucosa, and gastric ulcer. J Clin Gastroenterol. 2004; 39(1):50-5. View

16.

Price C, BOEKELHEIDE V . A synthesis of substituted 4-aminoquinolines. J Am Chem Soc. 2010; 68:1246-50. DOI: 10.1021/ja01211a031. View

17.

Rajanarendar E, Nagi Reddy M, Rama Krishna S, Rama Murthy K, Reddy Y, Rajam M . Design, synthesis, antimicrobial, anti-inflammatory and analgesic activity of novel isoxazolyl pyrimido[4,5-b]quinolines and isoxazolyl chromeno[2,3-d]pyrimidin-4-ones. Eur J Med Chem. 2012; 55:273-83. DOI: 10.1016/j.ejmech.2012.07.029. View

18.

ELDERFIELD R, GENSLER W . Synthesis of certain simple 4-aminoquinoline derivatives. J Am Chem Soc. 2010; 68:1250. DOI: 10.1021/ja01211a032. View

19.

Ratheesh M, Sindhu G, Helen A . Anti-inflammatory effect of quinoline alkaloid skimmianine isolated from Ruta graveolens L. Inflamm Res. 2013; 62(4):367-76. DOI: 10.1007/s00011-013-0588-1. View

20.

Riegel B, LAPPIN G . The preparation of some 4-aminoquinolines. J Am Chem Soc. 2010; 68:1229-32. DOI: 10.1021/ja01211a026. View