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Synthesis and antimicrobial evaluation of new glucosylimino thiazole derivatives

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Abstract

p-Sulphonic-N-propionyl aniline 3 was produced from sulphanilic acid with propionic acid under reflux for 2 h, then the compound 3 reacted with thionyl chloride and the corresponding imidoyl chloride 4 was obtained. When imidoyl chloride 4 reacted with potassium isothiocyanate and aniline, the corresponding thiourea derivatives 6 was produced. Compound 6 was reacted with tricyanovinylamine to produce the thiazole derivative 7 after cyclization. The microwave-assisted condensation of 2,3,4.6,-tetra-O-acetyl-β-D-glucopyranosylisothiocynate 8 with thiazole derivative 7 afforded the thiourea derivatives 9. Compound 10 a, b has been synthesized by reacting thiourea derivatives 9 with chloroacetone. The prepared compounds were screened for antibacterial properties against Staphylococcus aureus and Escherichia coli, and antifungal activity against Candida sp. The structure assignments of the new synthesized compounds are based on spectroscopic data.

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Acknowledgements

A. F. El-Farargy thanks Professor Norbert Krause, Lehrstuhl für Organische Chemie, TU Dortmund, for his repeated invitations, kind hospitality, and the facilities offered. The authors thank College of Science, Jouf University, Sakaka, Kingdom of Saudi and Chemistry Department and Faculty of Science, Zagazig University, Zagazig, Egypt for their continuous help and support.

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Authors and Affiliations

  1. Chemistry Department, College of Science, Jouf University, P.O. Box 2014, Sakaka, Jouf, Kingdom of Saudi Arabia

    Amira A. Ghoneim

  2. Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt

    Amira A. Ghoneim & Ahmed F. El-Farargy

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  1. Amira A. Ghoneim
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  2. Ahmed F. El-Farargy
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Correspondence to Amira A. Ghoneim.

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Ghoneim, A.A., El-Farargy, A.F. Synthesis and antimicrobial evaluation of new glucosylimino thiazole derivatives. J IRAN CHEM SOC 16, 1391–1399 (2019). https://doi.org/10.1007/s13738-019-01617-2

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  • DOI: https://doi.org/10.1007/s13738-019-01617-2

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