Anti-tubercular agents. Part 8: Synthesis, antibacterial and antitubercular activity of 5-nitrofuran based 1,2,3-triazoles

Kamal, Ähmed; Hussaini, S.M. Ali; Faazil, Shaikh; Poornachandra, Y.; Reddy, G. Narender; Kumar, C. Ganesh; Rajput, Vikrant Singh; Rani, C.; Khan, Inshad Ali; Babu, N. Jagadeesh

doi:10.1016/j.bmcl.2013.10.010

Cited by 42 publications

(21 citation statements)

References 32 publications

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“…16 Most of these compounds demonstrated excellent antibacterial, antimycobacterial and anti-biofilm activities. This propelled us to study the effect of structural modification on the antimicrobial activities of these compounds.…”

Section: Fig 1: Antimicrobial Agents In Marketmentioning

confidence: 99%

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Synthesis and antimicrobial potential of nitrofuran–triazole congeners

et al. 2015

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A series of 5-nitrofuran-triazole congeners were designed and synthesized by carrying out suitable structural modifications of the previously reported counterparts and were evaluated for their antimicrobial potential against both Gram-positive and Gram-negative bacterial strains. The compounds exhibited promising inhibition towards different Gram-positive pathogenic strains, while mild inhibitory effects were observed towards Gram-negative bacterial strains. Some of the compounds 9f, 9g, 9l and 9m were most active among the series, exhibiting a MIC value of 1.9 μg mL(-1) against different bacterial strains. The bactericidal activity was found to be in coherence with the bacterial growth inhibition data. The compounds were tested against fourteen different fungal strains and were found to possess excellent antifungal activities. Interestingly, all the compounds were equipotent to miconazole against one or more of the tested fungal strains and showed good activity against the other counterparts. A similar trend was observed in the case of their minimum fungicidal concentration values. Moreover, compound 9f exhibited two fold superior antifungal activity (MIC = 3.9 μg mL(-1)) than the standard miconazole (MIC = 7.8 μg mL(-1)) against C. albicans and C. parapsilosis. These compounds also effectively inhibited biofilm formation and compound 9f exhibited excellent anti-biofilm activity demonstrating a biofilm inhibitory concentration (BIC) as low as 0.8 μg mL(-1). A brief mechanistic study carried out on the most effective conjugate 9f indicated that it inhibits the ergosterol biosynthesis, thereby exhibiting antifungal effects. Molecular modelling studies carried out to study the binding modes of 9f correlates well with the antifungal activity and supported by ergosterol biosynthesis inhibition assay data. Most of these compounds exhibited ten times lower cytotoxicity toward the normal cells compared to the antimicrobial activity.

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Section: Fig 1: Antimicrobial Agents In Marketmentioning

confidence: 99%

“…This observation is completely in contrast with the antifungal activity of previously reported nitrofuran based triazole congeners from our laboratory. 16 …”

Section: Antimicrobial Activitymentioning

confidence: 99%

Synthesis and antimicrobial potential of nitrofuran–triazole congeners

et al. 2015

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“…1,2,3-Triazoles are an important class of heterocyclic compounds due to their wide usage as synthetic intermediates and pharmaceuticals [1][2][3]. Many triazole derivatives are found to exhibit various pharmacological properties such as antimicrobial [4], antiepileptic [5], antitubercular [6], and antibacterial [7], and a large number of 1,2,3-triazoles have also been reported with significant anticancer activities [8][9][10]. Since they are nontoxic, highly stable compounds and mostly water soluble, the 1,2,3-triazole derivatives could be ideal drug candidate and they could participate actively in molecular interactions by hydrogen bond formation [11] which implies their facility to binding with the biological targets [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Boukhssas

Aouine

Faraj

et al. 2017

Journal of Chemistry

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The compound, diethyl 1-((4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate 2, was synthesized in high yield, through 1,3-dipolar cycloaddition reaction of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and diethyl but-2-ynedioate in the absence of a solvent. The structure of the synthesized compound was established on the basis of NMR spectroscopy ( 1 H, 13 C), X-ray crystallography, and MS data. The prepared compound was also tested in vitro for its antibacterial activity against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). The calculation of MBC/MIC ratio showed that this triazole derivative 2 had a bactericidal effect on the two strains tested.

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“…Kamal et al. synthesized a series of nitrofuran‐based 1,2,3 triazole compounds, and identified compound 333 exhibiting activity with MIC value of 0.25 μg/mL that was four times higher that to standard anti‐TB drug linezolid (1 μg/mL) against M. tuberculosis H37Rv, and no cytotoxicity in two mammalian cell lines, namely MRC‐5 (normal lung cell line) and Vero (normal monkey kidney cell line) . Kim et al.…”

Section: Triazolesmentioning

confidence: 99%

New structural classes of antituberculosis agents

Kumar

Patel

Jain

2017

Medicinal Research Reviews

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Tuberculosis (TB), one of the deadliest diseases is shattering the health and socioeconomic status of the society. The emergence of multidrug resistant (MDR) and extremely drug resistant (XDR) strains has provided unprecedented lethal character to TB. The development of MDR and XDR strains of TB results in more deaths, longer duration of therapy, and appearance of the disease in the immunocompromised patients. Because of the development of rapid resistance by Mycobacterium tuberculosis, researchers are confronted with serious challenges in combating TB. For instance, the need for potency and specificity in therapeutic agents approaching clinics, and the increasing demand of low toxicity due to long duration of treatment. Recently, it is proposed that such challenges could be addressed by a shift from contemporary or known classes of drugs to new scaffold-containing or entirely new structural classes of drugs that possibly act on the previously unknown targets, resulting in possibly less instances of resistance development. The exploitation of advances made in the biology of TB in the last and present decades have created opportunities to discover a large number of new structural classes that specifically targets TB by molecular mechanism of action(s) unknown earlier. We have earlier reviewed new structural classes of anti-TB agents up to year 2005. This review covers literature reports of the subsequent 10 years on the discovery of new structural classes of synthetic anti-TB agents. Due to the availability of large number of research reports, we have divided new compounds in 38 structural classes, 368 structures, and 307 references.

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Anti-tubercular agents. Part 8: Synthesis, antibacterial and antitubercular activity of 5-nitrofuran based 1,2,3-triazoles

Cited by 42 publications

References 32 publications

Synthesis and antimicrobial potential of nitrofuran–triazole congeners

Synthesis and antimicrobial potential of nitrofuran–triazole congeners

Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

New structural classes of antituberculosis agents

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