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Microwave-assisted synthesis of double-headed derivatives of (4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-ethan-1-ol and study of their biological activity

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Abstract

The present investigation involves rapid and efficient synthesis of a series of some novel derivatives for 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethan-1-ol 5–21 using dl-malic acid under microwave (MW) irradiation. Reaction with several alkylating agents such as epichlorohydrin, 3-chloropropanol, (2-acetoxyethoxy) methyl bromide, propargyl bromide and chloroacetamide was studied. Not only higher yields but also shorter reaction times were observed in comparison with thermal procedure. Structures of the realized products have been established on the basis of their 1H/13C NMR, IR, elemental analysis and correlation experiments. It is well known that 1,2,4-triazole ring systems are famous for their antifungal activities, so the synthesized compounds were screened for their antifungal activities. The minimal inhibitory concentration (MIC) of the screened compounds exhibited prominent results against Gram (+ ve) and Gram ( − ve) and antifungal activities comparing with the standard drugs.

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Acknowledgements

The author presents great thanks to Institute of Bioorganic Chemistry, Hohenheim University, Stuttgart, Germany, for supplying me with the research facilities to achieve the practical experiments and analyses. The author is so much grateful to Dr. Zainab Fathy Elsawah in Pharmacology Department, Faculty of Pharmacy, Zagazig University for carrying out the biological activity section. I would also like to thank all the associated personnel in any used references.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt

    Reda A. Haggam

  2. Department of Chemistry, Faculty of Science, Islamic University, Almadinah Almonawara, Kingdom of Saudi Arabia

    Reda A. Haggam

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Haggam, R.A. Microwave-assisted synthesis of double-headed derivatives of (4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)-ethan-1-ol and study of their biological activity. Res Chem Intermed 47, 3733–3749 (2021). https://doi.org/10.1007/s11164-021-04501-y

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  • DOI: https://doi.org/10.1007/s11164-021-04501-y

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