Indole-chalcone linked 1,2,3-triazole hybrids: Facile synthesis, antimicrobial evaluation and docking studies as potential antimicrobial agents

Yadav, Monika; Lal, Kashmiri; Kumar, Aman; Kumar, Ashwani; Kumar, Devinder

doi:10.1016/j.molstruc.2022.132867

Cited by 35 publications

(16 citation statements)

References 59 publications

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“…In the last decade, interest in biologically active hybrids based on indole and various azoles has increased. For example, indole-functionalized isoxazoles [ 40 ], indole-imidazole [ 9 ], and indole-imidazolone [ 41 ] hybrids have anti-inflammatory properties, indole-oxadiazole hybrids are potential antidiabetic agents [ 42 ], and indole-chalcone linked 1,2,3-triazole hybrids exhibit antimicrobial activity [ 43 ]. A whole series of indole hybrids with azoles, such as pyrazole [ 44 ], thiazolidinone [ 45 ], isoxazoles [ 46 ], benzimidazole [ 47 ], and 1,2,4-triazole [ 48 ] showed potential antitumor and cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

2023

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Indoles and hydantoins are important heterocycles scaffolds which present in numerous bioactive compounds which possess various biological activities. Moreover, they are essential building blocks in organic synthesis, particularly for the preparation of important hybrid molecules. The series of hybrid compounds containing indoles and imidazolidin-2-one moiety with direct С─С bond were synthesized using an amidoalkylation one-pot reaction. All compounds were investigated as a growth regulator for germination, growth and development of wheat seeds (Triticum aestivum L). Their effect on drought resistance at very low concentrations (4 × 10−5 М) was evaluated. The study highlighted identified the leading compounds, 3a and 3e, with higher growth-regulating activity than the indole-auxin analogues.

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Section: Introductionmentioning

confidence: 99%

Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

2023

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“…C 4 carbon peak of triazole ring in 6a appeared at δ 142.81 ppm, while in 7a it is appeared at δ 142.58 ppm. The presence of all these peaks in synthesized compounds 13 C NMR spectra confirms the formation of triazoles [ 52 ].…”

Section: C Nmr Analysismentioning

confidence: 95%

“…A singlet at δ 8.62 ppm assigned to the –C = NH– proton [ 37 ]. Whereas, a confirmatory singlet was observed at δ 8.29 ppm is due to the triazolyl proton [ 52 ]. While, compound 7a showed a peak due to –NH proton of amide at δ 10.50 ppm, two singlets due to methylene protons were observed at δ 5.38 and δ 5.29 ppm.…”

Section: H Nmr Analysismentioning

confidence: 99%

Synthesis, antimicrobial evaluation and docking studies of fluorinated imine linked 1,2,3-triazoles

et al. 2022

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A diverse series of imine linked 1,2,3-triazole hybrids has been synthesized via Cu(I)-promoted click reaction, with an aim to develop some new antimicrobial molecules. The structural characterization of the synthesized triazole hybrids was accomplished using various spectral techniques like 1 H NMR, 13 C NMR, FTIR and HRMS. Among the synthesized hybrids, 7d exhibited highest antimicrobial efficacy against R. oryzae and S. aureus with MIC of 0.0123 µmol/mL and 0.0061 µmol/mL, respectively. Docking studies of the terminal alkynes ( 4a , 4b ) and triazole hybrids ( 6a , 6d , 7c , 7g ) showing high potency towards E. coli DNA gyrase and C. albicans sterol 14- α demethylase were also undertaken to understand the binding behaviour. Graphical abstract Supplementary Information The online version contains supplementary material available at 10.1007/s11164-022-04737-2.

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“…[29] Majority of the indole-chalcone tethered 1,2,3-triazole derivatives developed by M. Yadav et al exhibited excellent potency against the tested bacterial and fungal strains. [30] Further, M. Asad's group synthesized the chromonyl chalcone hybrids via green approach revealed to be highly potent antibacterial and antifungal agents. [31] So, a blend of two gifted structures dihydropyridine and chalcone can lead to the generation of a fascinating class of hetero-compounds exhibiting excellent biological activities.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antimicrobial Screening and Docking Studies of Newer 1,4‐Dihydropyridine tethered Chalcone Hybrids

Kumar¹,

Kumar

Upadhyay³

et al. 2022

ChemistrySelect

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The evolution of antimicrobial drug resistance demands the development of more effective therapeutics that are more potent with reduced side effects. In the present study, we reported the design and synthesis of 1,4-dihydropyridine clubbed with chalcone hybrids in excellent yields. Further, the biological assessment of these 1-phenyl-3-dihydropyridineprop-2-en-one chalcone hybrids as antimicrobial agents was accomplished against strains E.coli, Klebsiella pneumonia, Salmonella typhi, Staphylococcus aureus, Candida albicans (Yeast), Aspergillus niger, Alternaria solani and Fusarium oxy-sporum by well diffusion method in terms of zone of inhibition (in mm). Some Hybrids displayed the best anti-microbial activity against all the tested strains. A molecular docking study was performed for the most active compounds and showed the best binding pose with the highest binding score within the active sites of S. aureus DNA gyrase complexed with DNA and Lanosterol 14α-demethylase. These novel products evolved as promising leads for the future development of more potent anti-microbial compounds.

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Indole-chalcone linked 1,2,3-triazole hybrids: Facile synthesis, antimicrobial evaluation and docking studies as potential antimicrobial agents

Cited by 35 publications

References 59 publications

Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

Biologically Oriented Hybrids of Indole and Hydantoin Derivatives

Synthesis, antimicrobial evaluation and docking studies of fluorinated imine linked 1,2,3-triazoles

Design, Synthesis, Antimicrobial Screening and Docking Studies of Newer 1,4‐Dihydropyridine tethered Chalcone Hybrids

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