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Effective Microwave-Assisted Synthesis of 2-Chloro-5,6-dimethyl-3-(((substituted-benzylidene)hydrazono)methyl)-quinoline and Its Biological Assessment

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Abstract

ective: The quinoline scaffold is widely acknowledged as a critical framework for the development of novel pharmaceuticals. The derivatives of quinoline have antifungal, antibacterial, antitumor, and anticancer effects. Over the past 30 years, bacterial and fungal infections have grown significantly. Developing new infectious illness treatments is a major issue. As antimicrobials, we produced substituted 2-chloroquinoline compounds. The antimicrobial screening shows moderate activities against used microbes. Methods: By employing microwave irradiation, 2-chloro-5,6-dimethyl-3-(((substituted-benzylidene)hydrazono)methyl)quinoline can be synthesized quickly and efficiently. One-pot reaction between (E)-2-chloro-3-(hydrazonomethyl)-7,8-dimethylquinoline and substituted Carbaldehyde in glacial acetic acid and MeOH as a solvent yields the anticipated outcome. Results and Discussion: The MIC of produced compounds was determined by broth dilution. All fifteen (I–XV) synthesized compounds were evaluated for their antibacterial and antifungal activity in vitro. Compounds (I–VII), (X­–XIII), and (XIV) have greater antibacterial activity against Staphylococcus aureus and Streptococcus pyogenes Gram-positive bacteria, Compounds (IV), (VII), (XIII), (XIV), and (XV) have demonstrated effective antibacterial activity against Escherichia coli and Pseudomonas aeruginosa Gram-negative bacteria. Compounds (I), (IV), (V), and (XI) exhibited moderate antifungal activity against C. albicans, A. niger, and A. clavatus. Conclusions: A powerful one-pot approach has been designed to synthesize substituted quinolones. Microwave-assisted synthesis greatly accelerates reaction rate and reduces product impurityand shows modest in vitro antimicrobial and antifungal activity.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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ACKNOWLEDGMENTS

The Department of Chemistry at Saurashtra University, Rajkot, India, and the Centre of Excellence (CoE), NFDD Complex, Rajkot, India, who provided the laboratory space and spectral data, respectively, are gratefully acknowledged by the authors.

Funding

The funding for this work was supported by the institution’s regular resources, and no further grants were acquired.

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Authors and Affiliations

  1. Department of Chemistry, Saurashtra University, Rajkot, 360005, Gujarat, India

    N. K. Vegal, T. D. Bhatt, K. Kachhot & H. S. Joshi

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  1. N. K. Vegal
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  2. T. D. Bhatt
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  3. K. Kachhot
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  4. H. S. Joshi
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Contributions

The author NKV contributed to the writing and compilation processes of the manuscript and selected the literature data pertinent to the review topic under supervision of authors HSJ, KK, and TDB both made contributions to the literature study. Every author was present during the discussions.

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Correspondence to H. S. Joshi.

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This article does not contain any studies involving patients or animals as test objects. Informed consent was not required for this article. No conflict of interest was declared by the authors.

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Vegal, N.K., Bhatt, T.D., Kachhot, K. et al. Effective Microwave-Assisted Synthesis of 2-Chloro-5,6-dimethyl-3-(((substituted-benzylidene)hydrazono)methyl)-quinoline and Its Biological Assessment. Russ J Bioorg Chem 50, 239–250 (2024). https://doi.org/10.1134/S1068162024010254

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