Anti-mycobacterial, cytotoxic activities of Knoevenagel and (E)-α,β-unsaturated esters and ketones from 2-chloronicotinaldehydes

A facile synthesis of new 4,6‐dichloropyridine derivatives 5(a–f), 6(a–c), and 7(a–c) were synthesized using both conventional heating and solvent‐free microwave irradiation techniques. The results revealed that the latter method is superior to the conventional heating method. The easy work‐up of the products, rapid reaction, and mild conditions are noticeable features of this protocol. Structural elucidation of the synthesized compounds was made on the basis of various spectroscopic methods. The synthesized compounds were evaluated for their in vitro antimicrobial activity (minimum inhibitory concentration; MIC) against various microbial strains using the agar well‐diffusion method. Among the compounds, 5c showed best antimicrobial activity against most of the employed strains, especially against Staphylococcus aureus, Escherichia coli, Rhizopus arrhizus, and Candida albicans. Compounds 5a, 6a, 6c, 7a, and 7c showed significant antioxidant activity when compared to the other compounds. In addition to this, theoretical docking studies were performed for the highly potent compounds 5a, 6a, 6c, 7a, and 7c against three different drug targets belonging to the oxidoreductase family, and the results were found to be highly satisfactory.

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A Facile Synthesis of New 4,6‐Dichloropyridine Derivatives, Their Biological Evaluation for Antimicrobial and Antioxidant Activity, and Docking Studies

Singaram

Marimuthu²,

Baskaran³

et al. 2016

J Chinese Chemical Soc

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A facile synthesis of novel 5‐substituted pyridine 2 carboxamide derivatives and their biological evaluation and 3D QSAR studies

Dharman

Babu

Basha³

2018

J Chinese Chemical Soc

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A variety of novel 5‐substituted pyridine 2 carboxamides were designed and synthesized using both normal and solvent‐free microwave (MW) irradiation techniques. The results revealed that MW protocol proceeded smoothly under mild reaction conditions in short reaction times, thus avoiding the use of toxic organic solvents. Structural elucidation of the synthesized compounds was carried out on the basis of various spectroscopic methods, such as 1H NMR, 13C NMR, LCMS, and IR. The synthesized compounds were evaluated for their in vitro antimicrobial activity (MIC) using the agar disk diffusion method. Among the various synthetic compounds, compound 3b showed higher potential activity against Escherichia coli than the other compounds. The order of activity against E. coli of the studied compounds is 3b > 3e > 3g > 3h > 3d > 3c > 3a > 3f. Additionally, 2D and 3D structural features of the synthesized derivatives were recognized by the 3D‐QSAR model. This validated model exhibited good internal (r2, 0.924) and external prediction (r2pred, 0.851) correlation. The results of QSAR studies concluded that Alog P, the number of hydrogen bond acceptors, and the number of rotatable bonds were necessary features for the activity of the pyridine carboxamide derivatives.

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Anti-proliferative, structure–activity relationship of pyridinylchalcones and chromanones

et al. 2017

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Anti-mycobacterial, cytotoxic activities of Knoevenagel and (E)-α,β-unsaturated esters and ketones from 2-chloronicotinaldehydes

Cited by 7 publications

References 14 publications

A Facile Synthesis of New 4,6‐Dichloropyridine Derivatives, Their Biological Evaluation for Antimicrobial and Antioxidant Activity, and Docking Studies

A Facile Synthesis of New 4,6‐Dichloropyridine Derivatives, Their Biological Evaluation for Antimicrobial and Antioxidant Activity, and Docking Studies

A facile synthesis of novel 5‐substituted pyridine 2 carboxamide derivatives and their biological evaluation and 3D QSAR studies

Anti-proliferative, structure–activity relationship of pyridinylchalcones and chromanones

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