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Issue 6, 2018
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Synthesis and preliminary anti-inflammatory and anti-bacterial evaluation of some diflunisal aza-analogs

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Abstract

Our aim was to identify new multi-target compounds endowed with both anti-inflammatory and anti-bacterial activities for treatment of human infections. Diflunisal, a nonsteroidal anti-inflammatory agent, has recently been repurposed for its anti-virulence properties against methicillin-resistant Staphylococcus aureus. Effective synthesis of some aza-analogs of the anti-inflammatory drug diflunisal was carried out following the route involving key oxazole intermediates to obtain o- and m-hydroxypyridinecarboxylic acid derivatives. The newly synthesized diflunisal aza-analogs did not exhibit cytotoxic activity up to 80 μM and some of them exhibited anti-inflammatory activities, decreasing the levels of pro-inflammatory cytokines and prostaglandins induced by bacterial lipopolysaccharide in human primary macrophages. Ten of the diflunisal aza-analogs were found to have interesting antibacterial activity, sensitizing S. aureus, Streptococcus pyogenes, Enterococcus faecium, and Pseudomonas aeruginosa to the antibacterial effects of beta-lactam antibiotics and protein synthesis inhibitors.

Graphical abstract: Synthesis and preliminary anti-inflammatory and anti-bacterial evaluation of some diflunisal aza-analogs

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Article information


Submitted
13 Mar 2018
Accepted
14 Apr 2018
First published
24 Apr 2018

Med. Chem. Commun., 2018,9, 1017-1032
Article type
Research Article

Synthesis and preliminary anti-inflammatory and anti-bacterial evaluation of some diflunisal aza-analogs

D. Carta, P. Brun, M. Dal Pra, G. Bernabè, I. Castagliuolo and M. G. Ferlin, Med. Chem. Commun., 2018, 9, 1017
DOI: 10.1039/C8MD00139A

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