Synthesis and anti-mycobacterial activities of triazoloquinolones

Carta, Antonio; Palomba, Michele Francesco Luigi; Briguglio, Irene; Corona, Paola; Piras, Sandra; Jabès, Daniela; Guglierame, Paola; Molicotti, Paola; Zanetti, Stefania Anna Lucia

doi:10.1016/j.ejmech.2010.11.020

Cited by 29 publications

(20 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Two derivatives 30a and 30b have shown 100% growth inhibition at the MIC of 0.6 mM. In vitro cytotoxicity (IC 50 ) of 30a and 30b in the Vero cell line was found to be 0.45 mg/mL (SI: 2.27) and 0.21 mg/mL (SI: 1.05), respectively. SAR indicated that functionalities at both the quinoline (R 2 ) and arylhydrazone moiety (R 3 ) modulate the antimycobacterial activity.…”

Section: -Substituted Quinolinesmentioning

confidence: 99%

“…The presence of alkyl substituents at N-1 position was found to be more favorable for the activity than propenyl, benzyl or phenylethyl groups. Also, free carboxylic acid derivatives appeared to be superior compared to ester analogs 49,50 . Kantevari et al assessed the antimycobacterial activity of substituted aryl-tethered dihydro-6H-quinolin-5-ones (66), thiophenyl-tethered dihydro-6H-quinolin-5-ones (67) and their methyl hydroxyl analogs (68 and 69).…”

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

“…The SAR for the substituents at R 2 position follows activity order as: fused piperazines and piperidines4substituted piperidines (thio) morpholines4substituted piperazines 39 . (50). The CP derivatives showed moderate-to-excellent activity, with the MIC ranging from 1.21 to 10.82 nM when compared with ciprofloxacin and moxifloxacin (MIC: 6.04 and 1.94 nM, respectively).…”

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

“…The two compounds 37a and 37b exhibited an MIC of 3.2 and 3.5 mM, respectively, for M. tuberculosis H 37 Rv and showed better activity than ciprofloxacin (MIC: 4.7 mM) and ethambutol (MIC: 7.6 mM). The in vitro cytotoxicity (IC 50 ) of compounds 37a and 37b on mouse embryonic fibroblasts cell line (NIH 3T3) was reported as 1263 and 2050 mM, respectively, indicating that (Figure 7). The study was designed to evaluate the effect of (a) the introduction of conformational restriction in the rotation of the piperidinyl ring of mefloquine by the construction of an oxazolidine ring and (b) influence of substituted aryl/heteroaryl functions attached to the oxazolidine ring on the antimycobacterial activity (Figure 7).…”

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

“…For M. tuberculosis H 37 Rv, the CP-hydrazones appeared to be better (MIC: 1 mg/mL) than PAS-hydrazones and NF-hydrazones (MIC: 2-6 mg/mL). All hydrazones were found to be noncytotoxic for human hepatocytes, PBMC cells and human SH-SY5Y neuroblastoma cells (cytotoxic IC 50 . It is a hybrid of 4-amino-7-chloro-quinoline and ferrocene.…”

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

See 4 more Smart Citations

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Singh

Kaur

Mangla

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

Tuberculosis (TB) is still a major health concern worldwide. The increasing incidences of multi-drug-resistant tuberculosis (MDR-TB) necessitate the development of new anti-TB drugs acting via novel mode of action. The search of newer drugs for TB led to the identification of several quinoline-based antimycobacterial agents against both the drug-sensitive and MDR-TB. These agents have been designed by substituting quinoline scaffold with diverse chemical functionalities as well as by modifying quinoline/quinolone-based antibacterial drugs. Several of quinoline/quinolone derivatives displayed excellent antimycobacterial activity and were found free of cytotoxicity. This review highlights the critical aspects of design and structure-activity relationship of quinoline-and quinolone-based antimycobacterial agents.

show abstract

Section: -Substituted Quinolinesmentioning

confidence: 99%

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

Section: Quinoline Derivatives Derived From Drugsmentioning

confidence: 99%

See 3 more Smart Citations

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Singh

Kaur

Mangla

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

C7‐Regioselective C−H Fluorination of Benzotriazole Amides and Sulfonamides with NFSI under Metal‐Free Conditions

Li,

Fan,

Wang

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

The first metal‐free catalyzed C−H selective fluorination of benzotriazole amides and sulfonamide derivatives was achieved at the C‐7 position using NFSI (N‐fluorobenzenesulfonymide) as the fluorine source. The control experiment showed that the reaction underwent a free radical process that tolerated an excellent range of substrates with mild to good yields (>46 examples, yield up to 71 %).

show abstract

Quinoxaline‐based efflux pump inhibitors restore drug susceptibility in drug‐resistant nontuberculous mycobacteria

Corona

Ibba

Piras

et al. 2022

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

Nontuberculous mycobacteria (NTM) comprise several ubiquitous, environmentally localized bacteria that may be responsible for serious human diseases. NTMassociated pulmonary infections largely affect individuals with underlying respiratory disease or chronic disease and immunosuppressed patients. Mycobacterium simiae and M. abscessus are two NTMs responsible for lung disease in immunocompetent and immunocompromised individuals. In this study, two NTM strains were isolated from two patients admitted to an Italian hospital and were identified as M. simiae and M. abscessus. The two NTMs were tested for drug susceptibility against different antibiotics. To restore drug susceptibility, a new series of 2-aryl-3-phenoxymethylquinoxaline derivatives (QXs) was designed, synthesized, and investigated as efflux pump inhibitors (EPIs) against two clinical isolates of the above-cited NTMs, evaluating how EPIs can influence the drug minimal inhibitory concentration values and, therefore, the activity. The different\ resistance levels tracked in the clinical strains were reduced by EPIs, and in several cases, the susceptibility was completely restored. QXs also resulted as potential chemical probes to be used in drug susceptibility tests to identify the resistance origin when detected.

show abstract

Synthesis and anti-mycobacterial activities of triazoloquinolones

Cited by 29 publications

References 21 publications

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

Quinoline and quinolones: promising scaffolds for future antimycobacterial agents

C7‐Regioselective C−H Fluorination of Benzotriazole Amides and Sulfonamides with NFSI under Metal‐Free Conditions

Quinoxaline‐based efflux pump inhibitors restore drug susceptibility in drug‐resistant nontuberculous mycobacteria

Contact Info

Product

Resources

About