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Synthesis and Antimicrobial Activity of Some Novel 7-Chloro-4-aminoquinoline Derivatives

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Abstract

A number of novel 7-chloro-4-aminoquinoline derivatives have been efficiently synthesized by nucleophilic aromatic substitution reaction of 4,7-dichloroquinoline with α,ω-diaminoalkanes of variable carbon-chain length. Treatment of the intermediates with substituted aromatic/heteroaromatic aldehydes has led to the corresponding Schiff bases. Structures of the products have been elucidated from FTIR, 1H, and 13C NMR, and mass spectra. Antimicrobial tests of the compounds have indicated that the most active ones displayed MIC values in the range of 1.5 to 12.5 µg/mL, however they displayed no antifungal activity. According to the accumulated data, length of the carbon-chain linker and electronic properties of the compounds are decisive for their biological activity. Molecular docking studies have supported the above relationships.

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ACKNOWLEDGMENTS

The authors express sincere gratitude to the Department of Chemistry, Banasthali Vidyapith University, Banasthali, Rajasthan, India and the Central Drugs Research Institute (CDRI), Lucknow, India for rendering facilities of the sophisticated analytical instruments.

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Authors and Affiliations

  1. Division of Pharmaceutical Chemistry, Faculty of Pharmacy, Babu Banarasi Das Northern India Institute of Technology, Uttar Pradesh, 226028, Lucknow, India

    Gul Naz Fatima & Shailendra K. Saraf

  2. Department of Pharmacy, Banasthali Vidyapith, Banasthali, Rajasthan, 304022, Tonk, India

    Sarvesh K. Paliwal

Authors
  1. Gul Naz Fatima
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  2. Sarvesh K. Paliwal
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  3. Shailendra K. Saraf
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Correspondence to Shailendra K. Saraf.

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Fatima, G.N., Paliwal, S.K. & Saraf, S.K. Synthesis and Antimicrobial Activity of Some Novel 7-Chloro-4-aminoquinoline Derivatives. Russ J Gen Chem 91, 285–293 (2021). https://doi.org/10.1134/S1070363221020171

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