Microwave-assisted practical and simple method for heterocyclization of <i>o</i>-phenylenediamine and aldehydes using DDQ as oxidant agent

Naeimi, Hossein; Babaei, Zahra

doi:10.1080/17518253.2017.1314555

Cited by 9 publications

(1 citation statement)

References 34 publications

(27 reference statements)

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“…), 2‐amino benzothiazole ( 2 a , 1.1 equiv.) was stirred well along with catalytic amount of silica (50 mg) in dioxane as the solvent and finally irradiated under MW at 80–90 o C for 40–90 min, as DDQ already known as a versatile oxidative dehydrogenating agent besides tandem oxidative coupling‐cyclization reactions in one pot ,,. However, many side products with no desired product 3 a were formed during above tandem oxidative condensation reactions (Scheme , Method A).…”

Section: Resultsmentioning

confidence: 99%

Chemo‐Biocatalytic Oxidative Condensation of Natural Arylpropene with 2‐Aminobenzothiazole into Schiff‐Bases as Potent Anti‐Amyloid Agents: Studies Employing Transgenic C. elegans

et al. 2018

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Combining natural scaffolds with potent heterocyclic pharmacophores to have extra ordinary potency of synthetic hybrid molecules has gained significant attention as these compounds possess diverse biological activities including ameliorative effects against Alzheimer disease (AD) associated endpoints. In this context, a chemo-biocatalytic protocol has been described wherein 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) catalyzed oxidation of natural methoxylated phenylpropenes into corresponding cinnamaldehydes followed by Bovine serum albumin (BSA)-catalyzed condensation reaction with heterocyclic amine in water provides a series of Schiff bases in moderate to good yield. Interestingly, some of the 2-aminobenzothiazole based Schiff bases with dioxymethylene substituted cinnamaldehydes, an oxidized product of natural isosafrole, appear as an multifunctional agents which significantly decreased the disease associated endpoints in C. elegans model of Alzheimer's disease. These Schiff bases exerted their effect by reducing Ab aggregation, decreasing lipid deposition and oxidative stress, thereby preventing cholinergic neuronal degeneration. All these properties highlight the therapeutic potential of these prototypes to be developed as new multifunctional drug candidates in the treatment of Alzheimer's disease. Moreover, molecular modeling studies have revealed the interaction of Schiff base with acetylcholine receptors.

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Section: Resultsmentioning

confidence: 99%

Chemo‐Biocatalytic Oxidative Condensation of Natural Arylpropene with 2‐Aminobenzothiazole into Schiff‐Bases as Potent Anti‐Amyloid Agents: Studies Employing Transgenic C. elegans

et al. 2018

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One‐pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies

Ersan

Yüksel

Ertan-Bolelli

et al. 2020

J Chinese Chemical Soc

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In an attempt to design a greener approach for the synthesis of a potent class of antimicrobials, 1,2‐phenylenediamine derivatives were reacted with various 1/2‐carboxylic acid‐substituted naphthalene derivatives to generate a series of naphthyl‐substituted benzimidazole derivatives (11–19) using polyphosphoric acid as catalyst under microwave irradiation and conventional synthesis method. This is an eco‐friendly and swift reaction method for a synthetic approach to diverse benzimidazoles. Structures of the synthesized compounds were established on the basis of spectral data and they were screened for their antimicrobial activity. Compound 18 showed maximum potency against all Gram‐positive and Gram‐negative bacterial strains with a minimum inhibitory concentration (MIC) value in the range of 7.81–62.50 μg/ml. Only compound 17 was found to be the most active against all fungal strains with a MIC value of 15.62 μg/ml. In this study, we performed molecular docking experiments to understand the interactions between compounds 17 and 18 and E. coli topoisomerase I, and we compared the results obtained with that of 2‐(3,4‐dimethoxyphenyl)‐5‐[5‐(4‐methylpiperazin−1‐yl)‐1H‐benzimidazol‐2‐yl]‐1H‐benzimidazole (DMA). Compounds 17 and 18 demonstrated strong interactions with important active site residues, similar to DMA. As a result, the compounds obtained from this study can be used in designing new potent inhibitors of E. coli topoisomerase I.

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Microwave-assisted C N formation reactions

Molnár

2021

Green Sustainable Process for Chemical and Environmental Engineering and Science

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Microwave-assisted practical and simple method for heterocyclization of o-phenylenediamine and aldehydes using DDQ as oxidant agent

Cited by 9 publications

References 34 publications

Chemo‐Biocatalytic Oxidative Condensation of Natural Arylpropene with 2‐Aminobenzothiazole into Schiff‐Bases as Potent Anti‐Amyloid Agents: Studies Employing Transgenic C. elegans

Chemo‐Biocatalytic Oxidative Condensation of Natural Arylpropene with 2‐Aminobenzothiazole into Schiff‐Bases as Potent Anti‐Amyloid Agents: Studies Employing Transgenic C. elegans

One‐pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies

Microwave-assisted C N formation reactions

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