A green synthesis of quinoline‐4‐carboxylic derivatives using p‐toluenesulfonic acid as an efficient organocatalyst under microwave irradiation and their docking, molecular dynamics, ADME‐Tox and biological evaluation

P‐Toluenesulfonic acid, being an efficient, nonhazardous, and fast accessible organocatalyst, was used for the preparation of quinoline‐4‐carboxylic acid derivatives via a one‐pot three‐component reaction of aromatic benzaldehyde, substituted aniline, and pyruvic acid under microwave irradiation. Af...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2020-04, Vol.57 (4), p.1524-1544
Main Authors: Patel, Dhaval B., Rajani, Dhanji P., Rajani, Smita D., Patel, Hitesh D.
Format: Article
Language:English
Subjects:
Acids
Aniline
Benzaldehyde
Biological activity
Carboxylic acids
Chemical synthesis
Column chromatography
Derivatives
E coli
Fungicides
Irradiation
Molecular docking
Molecular dynamics
Quinoline
Reaction time
Solvents
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Summary:P‐Toluenesulfonic acid, being an efficient, nonhazardous, and fast accessible organocatalyst, was used for the preparation of quinoline‐4‐carboxylic acid derivatives via a one‐pot three‐component reaction of aromatic benzaldehyde, substituted aniline, and pyruvic acid under microwave irradiation. After completion of the reaction, the pure products were isolated by column chromatography. Here, to achieve the desired synthesis, various catalytic and solvent conditions were applied to perform a comparison study. We are using higher yield, simple work‐up process, avoiding the use of hazardous organic solvents, short reaction time and higher advantages of the present protocol in the study. Biological activities of synthesized compounds were tested against various antibacterial, antifungal, antimalarial, and antituberculosis strains. Compounds 4a and 4c (MIC 50 μg/mL) and compounds 4d and 4n (MIC 62.5 μg/mL) were found active against the Escherichia coli strain, compounds 4c and 4p (MIC 25 μg/mL) were found active against the Staphylococcus aureus strain, and compounds 4c and 4d were found active against the Plasmodium falciparum strain. Molecular docking revealed that ligands and proteins fitted exactly in the binding pocket and had significant correlation with the biological activity. We have also tested molecular dynamics and ADME‐Tox parameters for the synthesized compounds.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3848