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Upstream product

• 1571-30-8 8-hydroxy-quinoline-2-carboxylic acid 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Ring-substituted 8-hydroxyquinoline-2-carboxanilides as photosystem II inhibitors

Ring-substituted 8-hydroxyquinoline-2-carboxanilides inhibited photosynthetic electron transport (PET) through photosystem (PS) II. Their inhibitory efficiency depended on the compound lipophilicity, the electronic properties of the substituent R and the

Activity of ring-substituted 8-hydroxyquinoline-2-carboxanilides against intestinal sulfate-reducing bacteria Desulfovibrio piger

Desulfovibrio genus is dominant among sulfate-reducing bacteria (SRB) in the large intestine of healthy people and animals. It is mostly isolated from patients with inflammatory bowel disease (IBD) and can be involved in the disease initiation. Primary in vitro screening of 8-hydroxyquinoline-2-carboxanilides was performed against Desulfovibrio piger Vib-7 representing SRB. The most effective compounds with MIC90/MBC values in the range of 17–23 μM/20–23 μM, respectively, were substituted in C’(3) by CF3, OCH3, CH3 and in C’(4) by CF3. Their activity was twofold higher than that of ciprofloxacin. These compounds did not express any significant cytotoxic effect on THP-1 cells up to the tested concentration of 30 μM. The antibacterial efficacy of the most active C’(3)-substituted compounds practically did not change with increasing compound lipophilicity, indicating that this position of substitution is favorable for significant antimicrobial effect, while the antibacterial activity of most of C’(2) and C’(4)-substituted derivatives decreased linearly with increasing compound lipophilicity. In addition, the dependence of activity on electronic Hammett’s σ parameter of the substituent R was quasi-parabolic for the most effective C’(3)-substituted compounds.

Ring-substituted 8-hydroxyquinoline-2-carboxanilides as potential antimycobacterial agents

In this study, a series of twenty-two ring-substituted 8-hydroxyquinoline-2-carboxanilides was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Mycobacterium tuberculosis H37Ra, Mycobacterium avium complex and M. avium subsp. paratuberculosis. Some of the tested compounds showed the antimycobacterial activity against M. avium subsp. paratuberculosis comparable with or higher than that of rifampicin. 8-Hydroxy-N-[3-(trifluoromethyl)phenyl]- and 8-hydroxy-N-[4-(trifluoromethyl)phenyl]quinoline-2-carboxamide showed MIC = 24 μM against all tested mycobacterial strains. 3-Methoxyphenyl- and 3-methylphenyl derivatives expressed MIC = 27 or 29 μM also against all the tested strains. Their activity against M. avium subsp. paratuberculosis was 4-fold higher than that of rifampicin. 2-Bromophenyl- and 2-(trifluoromethyl)phenyl derivatives had MIC = 23 or 24 μM against M. tuberculosis. A significant decrease of mycobacterial cell metabolism (viability of M. tuberculosis H37Ra) was observed using MTT assay. Screening of cytotoxicity of the compounds was performed using the THP-1 cells, and no significant lethal effect was observed up to tested concentration 30 μM. The structure-activity relationships are discussed.