Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases

Aouad, Mohamed Reda

doi:10.5935/0103-5053.20150196

Cited by 11 publications

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“…As continuation of our previous study directed to design novel 1,4,5-trisubstituted-1,2,3-triazoles [ 34 , 35 , 36 ], we have adopted the optimized ecofriendly solvent free click procedure previously developed in our laboratory for the elaboration of two novel 4,5-diester-1,2,3-triazoles carrying benzothiazole-piperazine conjugate. The reaction required 1,3-dipolar cycloaddition reaction between the azide 3 with dimethyl/diethylacetylene dicarboxylate under neat conditions, in a water bath for 3 min, to afford the desired dimethyl/diethyl 1-(2-(4-(benzothiazol-2-yl)piperazin-1-yl)-2-oxoethyl)-1 H -1,2,3-triazole-4,5-dicarboxylate ( 6a , b ) in 92–94% yields.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Anticancer Screening of Novel Benzothiazole-Piperazine-1,2,3-Triazole Hybrids

et al. 2018

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A library of novel regioselective 1,4-di and 1,4,5-trisubstituted-1,2,3-triazole based benzothiazole-piperazine conjugates were designed and synthesized using the click synthesis approach in the presence and absence of the Cu(I) catalyst. Some of these 1,2,3-triazole hybrids possess in their structures different heterocyclic scaffold including 1,2,4-triazole, benzothiazole, isatin and/or benzimidazole. The newly designed 1,2,3-triazole hybrids were assessed for their antiproliferative inhibition potency against four selected human cancer cell lines (MCF7, T47D, HCT116 and Caco2). The majority of the synthesized compounds demonstrated moderate to potent activity against all the cancer cell lines examined. Further, we have established a structure activity relationship with respect to the in silico analysis of ADME (adsorption, distribution, metabolism and excretion) analysis and found good agreement with in vitro activity.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Anticancer Screening of Novel Benzothiazole-Piperazine-1,2,3-Triazole Hybrids

et al. 2018

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“…Based on the above observations and by taking the advantages of MW, we herein report the click synthesis of novel benzothiazole based 1,2,3-triazole moiety by both conventional and microwave irradiation as a valuable addition to our interest on the development of new polyheterocyclic compounds [21][22][23][24][25][26][27][28][29]. Microwave technique has been used in this study because it improves reaction rates, environmentally friendly and operational simplicity [30].…”

Section: Introductionmentioning

confidence: 97%

Green microwave versus conventional synthesis, crystal structure of 1-(4-(Benzothiazol-2-yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethenone and HS-Analysis

Said

Messali

Rezki

et al. 2020

Journal of Taibah University for Science

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This study reports an efficient eco-friendly microwave assisted synthesis of 1-(4-(benzothiazol-2yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (4) through the click cyclocondensation of 2-azido-1-(4-(benzo[d]thiazol-2-yl)piperazin-1-yl)ethanone (3) with phenyl acetylene. The synthesis was carried out under optimized copper catalyst copper(II) sulfate pentahydrate/sodium ascorbate, t-BuOH/water (1:1, v/v) to afford the regioselective 1,4-disubstituted 1,2,3-triazole isomer. The reactions were greatly accelerated using microwave irradiation. The new designed 1,2,3-triazole was fully characterizid by IR, NMR, MS spectral data and X-ray diffraction. The crystal structure of 4 demonstrated a conventional chair conformation for the piperazine ring. Interesting Hirshfeld Surface Analysis (HAS) was conducted showing clear agreement with the XRD analysis.

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“…This inspired us to synthesize new SBs clubbed to a 1,2,3-triazole core and chemically characterized using DFT calculations. Possible biological applications were also predicated by exploiting molecular docking and cytotoxicity, using computer-aided online software, as a continuation of our interest in developing novel bioactive heterocyclic-based SB linkages [ 25 , 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

New 1,2,3-Triazole Scaffold Schiff Bases as Potential Anti-COVID-19: Design, Synthesis, DFT-Molecular Docking, and Cytotoxicity Aspects

et al. 2021

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Schiff bases encompassing a 1,2,3-triazole motif were synthesized using an efficient multi-step synthesis. The formations of targeted Schiff base ligands were confirmed by different spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, and CHN analysis). The spectral data analysis revealed that the newly designed hydrazones exist as a mixture of trans-E and cis-E diastereomers. Densityfunctional theory calculations (DFT) for the Schiff bases showed that the trans-trans form has the lowest energy structure with maximum stability compared to the other possible geometrical isomers that could be present due to the orientation of the amidic NH–C=O group. The energy differences between the trans-trans on one side and syn-syn and syn-trans isomers on the other side were 9.26 and 5.56 kcal/mol, respectively. A quantitative structure-activity relationship investigation was also performed in terms of density functional theory. The binding affinities of the newly synthesized bases are, maybe, attributed to the presence of hydrogen bonds together with many hydrophobic interactions between the ligands and the active amino acid residue of the receptor. The superposition of the inhibitor N3 and an example ligand into the binding pocket of 7BQY is also presented. Further interesting comparative docking analyses were performed. Quantitative structure-activity relationship calculations are presented, illustrating possible inhibitory activity. Further computer-aided cytotoxicity analysis by Drug2Way and PASS online software was carried out for Schiff base ligands against various cancer cell lines. Overall, the results of this study suggest that these Schiff base derivatives may be considered for further investigation as possible therapeutic agents for COVID-19.

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Efficient Eco-Friendly Solvent-Free Click Synthesis and Antimicrobial Evaluation of New Fluorinated 1,2,3-Triazoles and their Conversion into Schiff Bases

Cited by 11 publications

References 0 publications

Design, Synthesis and Anticancer Screening of Novel Benzothiazole-Piperazine-1,2,3-Triazole Hybrids

Design, Synthesis and Anticancer Screening of Novel Benzothiazole-Piperazine-1,2,3-Triazole Hybrids

Green microwave versus conventional synthesis, crystal structure of 1-(4-(Benzothiazol-2-yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethenone and HS-Analysis

New 1,2,3-Triazole Scaffold Schiff Bases as Potential Anti-COVID-19: Design, Synthesis, DFT-Molecular Docking, and Cytotoxicity Aspects

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