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Synthesis and biological evaluation of new [1,3,4]thiadiazepino[7,6-b]quinolin-2-amines as potent anti-microbial agents

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Abstract

Four series of 56 new thiadiazepinoquinoline amines were synthesized and characterized by spectroscopic techniques (NMR, IR, and MS) and elemental analysis. All the compounds were screened for in vitro anti-microbial activity. Highest inhibitory activity (MIC of 0.03 mg/ml) was exerted by 2e against Bacillus subtilis and Streptococcus pyogenes, 2f against Escherichia coli and Streptococcus pyogenes, and 4k against only Bacillus subtilis. Only compounds 1g and 2g revealed potent anti-fungal activity (MIC 0.03 mg/ml) compared to the standard against Alternaria alternata. Most of the compounds exhibited better anti-bacterial activity than anti-fungal activity against the microorganisms employed in this study. These studies suggest that the thiadiazepinoquinoline scaffold may serve as a new promising template for further elaboration as anti-bacterial and anti-fungal drugs.

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Acknowledgments

Authors are grateful to HEJ research Institute of Chemistry, University of Karachi, Pakistan, for the spectral analysis.

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Authors and Affiliations

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

    Hasnain Muhammad Raza, Nada-E-Ali Rizvi & Hamid Latif Siddiqui

  2. Institute of Agricultural Sciences, University of the Punjab, Lahore, Pakistan

    Arshad Javaid

  3. National Institute of Biotechnology and Genetic Engineering, Faislabad, 38000, Pakistan

    Mazhar Iqbal

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  1. Hasnain Muhammad Raza
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  2. Nada-E-Ali Rizvi
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  3. Hamid Latif Siddiqui
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  4. Arshad Javaid
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  5. Mazhar Iqbal
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Correspondence to Hasnain Muhammad Raza.

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Raza, H.M., Rizvi, NEA., Siddiqui, H.L. et al. Synthesis and biological evaluation of new [1,3,4]thiadiazepino[7,6-b]quinolin-2-amines as potent anti-microbial agents. Med Chem Res 22, 4001–4015 (2013). https://doi.org/10.1007/s00044-012-0389-z

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