Synthesis, antimicrobial evaluation and docking studies of oxazolone-1,2,3-triazole-amide hybrids

Kumar, Lokesh; Lal, Kashmiri; Kumar, Aman; Kumar, Ashwani

doi:10.1007/s11164-021-04588-3

Cited by 15 publications

(4 citation statements)

References 46 publications

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“…It is important methodology for drug design and construction of multitarget‐based lead molecules [43] . The triazole ring contains an important isostere of Schiff base, [44] pyrazoline, [45] imidazole, [46] oxazole, [47] pyrrole, [48] thiazole [49] and amide moiety [50] etc . in designing various types of drug like compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial and In Silico Studies of Isatin Schiff Base Linked 1,2,3‐Triazole Hybrids

Kumar,

Bhukal,

Raman

et al. 2024

Chemistry & Biodiversity

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A new series of isatin‐Schiff base linked 1,2,3‐triazole hybrids has been synthesized using CuAAC approach from (E)‐3‐(phenylimino)‐1‐(prop‐2‐yn‐1‐yl)indolin‐2‐one derivatives in high yield (73‐91 %). These synthesized derivatives were characterized using FT‐IR, 1H NMR, 13C NMR, 2D‐NMR and HRMS spectral techniques. The in vitro antimicrobial activity assay proposed that most of the tested hybrids exhibited promising activity. Compound 5j displayed good significant antibacterial efficacy against P. aeruginosa and B. subtilis with MIC value of 0.0062 µmol/mL. While, 5j showed better antifungal potency against A. niger with MIC value of 0.0123 µmol/mL. The docking studies of most promising compounds were also performed with the well‐known antibacterial and antifungal targets i.e. 1KZ1, 5TZ1. Molecular modelling investigations demonstrated that hybrids 5h and 5l exhibited good interactions with 1KZN and 5TZ1, with binding energies of ‐9.6 and ‐11.0 kcal/mol, respectively. Further, molecular dynamics studies of the compounds showing promising binding interactions were also carried out to study the stability of complexes of these hybrids with both the targets.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial and In Silico Studies of Isatin Schiff Base Linked 1,2,3‐Triazole Hybrids

Kumar,

Bhukal,

Raman

et al. 2024

Chemistry & Biodiversity

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“…At present, the chemical structure of SDHIs on the market all contain amide bonds, so they are also called amide pesticides. Many studies have shown that amides had broad-spectrum antibacterial, [29][30][31] antiviral, 32 insecticidal 33 and herbicidal 34,35 activities. They were widely used in agricultural production such as methuroxam and fludixamide (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antibacterial and antifungal activity of myricetin derivatives containing piperidine and amide fragments

Zhang

Feng

Chen

et al. 2023

Pest Management Science

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BACKGROUNDContinuous use of synthetic bactericides and fungicides is causing pathogens to develop resistance, resulting in increased use of pesticides and affecting food security. The green pesticides derived from natural products could reduce or avoid ‘pesticide hazards’ caused by synthetic pesticides as a result of their unique mechanism of action. Therefore, it is of great significance to create green pesticides with novel structures.RESULTSHerein, 30 novel myricetin derivatives containing piperidine and amide fragments were designed and synthesized using active group splicing. Among them, compound Z30 had excellent inhibitory effect against Xanthomonas oryzae pv. Oryzae (Xoo) with the half effective concentration (EC50) of 2.7 μg mL−1. Compound Z26 not only exhibited better antibacterial activity against Xaxonopodis pv. Citri (Xac) with EC50 of 3.9 μg mL−1, but also displayed higher antifungal activity against Rhizoctonia solani (Rs) with EC50 of 8.3 μg mL−1. In vivo experiments proved that Z30 against bacterial blight of rice and Z26 against rice blast exhibits significant protective and curative effect. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) showed that Z26 and Z30 could change the integrity of cell wall and membrane of pathogen Xoo, Xac and Rs, resulting in cytoplasmic leakage and eventually death. Enzymatic assay, molecular docking and molecular dynamics simulations (MDs) indicated that Z26 could be used as a potential succinate dehydrogenase inhibitor (SDHI).CONCLUSIONZ26 and Z30 significantly reduced the pathogenicity of the pathogens, which provided a new idea and direction for the development of green pesticides. © 2023 Society of Chemical Industry.

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“…Their derivatives have shown promise as antifungal agents, primarily by impeding the synthesis of ergosterol, a key constituent of the fungal cell membrane [12,13].This inhibition is achieved through the suppression of the fungal cytochrome P450 enzyme, ultimately resulting in fungal apoptosis [14]. Moreover, azole based compounds possess various biological activity such as, anticonvulsants, antidepressants, antioxidants, antiinflammatory agents, antibiotics, anti-fungal agents, antiviral agents, and so on [15]. Triazole compounds, including fluconazole, itraconazole, voriconazole [16], posaconazole, albaconazole, efinaconazole, ravuconazole, and isavuconazole, have garnered significant interest within the field of azole drugs [17].This heightened attention can be attributed to their wider range of effectiveness, favorable pharmacokinetic properties, selectivity, and satisfactory safety profile [18].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Pharmacologically Important 1,2,4-Triazoles as Promising Antifungal Agents against Candida Albicans

Raafat,

Ali,

Abuo-Rahma

2023

Octahedron Drug Research

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Synthesis, antimicrobial evaluation and docking studies of oxazolone-1,2,3-triazole-amide hybrids

Cited by 15 publications

References 46 publications

Synthesis, Characterization, Antimicrobial and In Silico Studies of Isatin Schiff Base Linked 1,2,3‐Triazole Hybrids

Synthesis, Characterization, Antimicrobial and In Silico Studies of Isatin Schiff Base Linked 1,2,3‐Triazole Hybrids

Synthesis, antibacterial and antifungal activity of myricetin derivatives containing piperidine and amide fragments

Recent Advances in Pharmacologically Important 1,2,4-Triazoles as Promising Antifungal Agents against Candida Albicans

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