Design, synthesis and 3D-QSAR studies of new diphenylamine containing 1,2,4-triazoles as potential antitubercular agents

Krishna, Kala; Inturi, Bharathkumar; Pujar, Gurubasavaraj V.; Purohit, Madhusudan; Vijaykumar, Gowdara Shankarappa

doi:10.1016/j.ejmech.2014.07.051

Cited by 72 publications

(47 citation statements)

References 27 publications

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“…Compound ( 38a ) depicted anti‐TB activity (0.2 μ m ) which is comparable to that of the standard drug INH (<0.2 μ m ) and possesses benzylidene amino group at position 4‐ and morpholino methyl group at position 2‐ of the 1,2,4‐triazole ring system. Compounds with substituted phenyl ring at position 4‐ of the 1,2,4‐triazoles confirmed reduced activity compared to unsubstituted counterparts ( 38a ) (Figure ).…”

Section: 24‐triazole Derivatives For Treatment Of Tuberculosismentioning

confidence: 89%

Triazole: A Promising Antitubercular Agent

et al. 2015

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Tuberculosis is a contagious disease with comparatively high mortality worldwide. The statistics shows that around three million people throughout the world die annually from tuberculosis and there are around eight million new cases each year, of which developing countries showed major share. Therefore, the discovery and development of effective antituberculosis drugs with novel mechanism of action have become an insistent task for infectious diseases research programs. The literature reveals that, heterocyclic moieties have drawn attention of the chemists, pharmacologists, microbiologists, and other researchers owing to its indomitable biological potential as anti-infective agents. Among heterocyclic compounds, triazole (1,2,3-triazole/1,2,4-triazole) nucleus is one of the most important and well-known heterocycles, which is a common and integral feature of a variety of natural products and medicinal agents. Triazole core is considered as a privileged structure in medicinal chemistry and is widely used as 'parental' compounds to synthesize molecules with medical benefits, especially with infection-related activities. In the present review, we have collated published reports on this versatile core to provide an insight so that its complete therapeutic potential can be utilized for the treatment of tuberculosis. This review also explores triazole as a potential targeted core moiety against tuberculosis and various research ongoing worldwide. It is hoped that this review will be helpful for new thoughts in the quest for rational designs of more active and less toxic triazole-based antituberculosis drugs.

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Section: 24‐triazole Derivatives For Treatment Of Tuberculosismentioning

confidence: 89%

Triazole: A Promising Antitubercular Agent

et al. 2015

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“…Various isonicotinic acid derivatives like isonicotinyl hydrazides [32] , isonicotinamide derivatives [33] , 1,2,4-triazoles from isonicotinic acid hydrazide [34] , novel nalidixic acid derived 1,2,4-triazole [35] , 5-mercapto-1,2,4-triazole, novel 4H-1,2,4-triazol-3-yl-cycloalkanols [36] , new imidazole and 1,2,4-triazole substituted fluorobenzimidazoles [37] , and diphenylamine containing 1,2,4-triazoles [38] , have been reported to possess diverse activity including antimicrobial and antitubercular. The therapeutic potential of 1,2,4-triazole prompted us to synthesize new compounds in which substituent could be arranged in a pharmacophoric pattern to display high order of antimycobacterial activity.…”

Section: Research Papermentioning

confidence: 99%

Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents

Singh¹,

Kashaw²,

Mishra³

et al. 2018

pharmaceutical-sciences

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“…The 1,2,4-triazoles are considered an important nucleus that is associated with numerous biological activities, such as herbicidal [4][5][6], antifungal [7][8][9], antiviral [10], GHS-R1a ghrelin receptor [11], antimicrobial [12], anticancer [13], anticonvulsant [14], and antitubercular activities [15]. In addition, Diniconazole, Triadimefon, Triadimenol, Flusilazole, Fluconazole, Itraconazole, which have a 1,2,4-triazole moiety, appear to be very effective.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, DFT Study and Antifungal Activity of 4-(5-((4-Bromobenzyl) thio)-4-Phenyl-4H-1,2,4-Triazol-3-yl)pyridine

Zhai

Yang

et al. 2015

Crystals

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Abstract:The title compound 4-(5-((4-bromobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine (C 20 H 15 BrN 4 S) was synthesized, and its structure was confirmed by 1 H NMR, MS and elemental analyses and single-crystal X-ray structure determination. It crystallizes in the triclinic space group P-1 with a = 7.717(3), b = 9.210(3), c = 13.370(5) Å, α = 80.347(13), β = 77.471(13), γ = 89.899(16)˝, V = 913.9(6) Å 3 , Z = 2 and R = 0.0260 for 3145 observed reflections with I > 2σ(I). A Density functional theory (DFT) (B3LYP/6-31G) calculation of the title molecule was carried out. The full geometry optimization was carried out using a 6-31G basis set, and the frontier orbital energy. Atomic net charges are discussed. Calculated bond lengths and bond angles were found to differ from experimental values, and the compound exhibits moderate antifungal activity.

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Design, synthesis and 3D-QSAR studies of new diphenylamine containing 1,2,4-triazoles as potential antitubercular agents

Cited by 72 publications

References 27 publications

Triazole: A Promising Antitubercular Agent

Triazole: A Promising Antitubercular Agent

Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents

Synthesis, Crystal Structure, DFT Study and Antifungal Activity of 4-(5-((4-Bromobenzyl) thio)-4-Phenyl-4H-1,2,4-Triazol-3-yl)pyridine

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