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Antioxidant and antimicrobial studies of novel N′-(substituted-2-chloroquinolin-3-yl)methylidene-4-hydroxy-2H-1,2-benzothiazine-3-carbohydrazides 1,1-dioxides

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Abstract

N′-(2-Chloroquinolin-3-yl)methylidene-4-hydroxy-2H-1,2-benzothiazine-3-carbohydrazides 1,1-dioxide (4a–4j) were prepared starting from corresponding methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate (1a and 1b) by condensation with hydrazine hydrate, followed by treatment with substituted 2-chloro-3-formyl quinolines (3a–3e) under ultrasonic irradiation. On the other hand, substituted 2-chloro-3-formyl quinolines were prepared in a facile way from respective acetanilides under microwave irradiation in very short duration of time (1.5–3.0 min) obtaining excellent yields. The compounds (4a–4j) were tested for their superoxide scavenging and antimicrobial activities. Almost all the compounds showed moderate superoxide scavenging activity and compounds 4a, 4d, 4g, and 4j were found active against gram-positive bacterial strains. In addition, 4a, 4e, and 4i were active against fungi (Aspergillus flavus, Aspergillus niger, Fusarium oxysporum).

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Acknowledgments

The authors (MA, SUFR and HLS) are grateful to Higher Education Commission, Pakistan for financial assistance. We are also thankful to International Centre for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi and Institute of Chemistry, University of the Punjab for research facilities, spectral measurements and antioxidant studies.

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Authors and Affiliations

  1. Institute of Chemistry, University of the Punjab, Lahore, 54590, Pakistan

    Matloob Ahmad, Syed Umar Farooq Rizvi & Hamid Latif Siddiqui

  2. Applied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpur Road, Lahore, 54600, Pakistan

    Matloob Ahmad

  3. Department of Chemistry, Gomal University, Dera Ismail Khan, Pakistan

    Saeed Ahmad

  4. Department of Chemistry, University of Calgary, 2500 University Drive, N. W. Calgary, Calgary, AB, T2N 1N4, Canada

    Masood Parvez

  5. Department of Mycology and Plant Pathology, University of the Punjab, Lahore, Pakistan

    Ruqia Suliman

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  1. Matloob Ahmad
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  2. Syed Umar Farooq Rizvi
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  3. Hamid Latif Siddiqui
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  4. Saeed Ahmad
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  5. Masood Parvez
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Correspondence to Hamid Latif Siddiqui.

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Ahmad, M., Rizvi, S.U.F., Siddiqui, H.L. et al. Antioxidant and antimicrobial studies of novel N′-(substituted-2-chloroquinolin-3-yl)methylidene-4-hydroxy-2H-1,2-benzothiazine-3-carbohydrazides 1,1-dioxides. Med Chem Res 21, 2340–2348 (2012). https://doi.org/10.1007/s00044-011-9755-5

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  • DOI: https://doi.org/10.1007/s00044-011-9755-5

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