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Microwave-assisted and thermal synthesis of nanosized thiazolyl-phenothiazine derivatives and their biological activities

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Abstract

Efficient synthesis of a series of nanosized phenothiazine derivatives incorporating thiazole moiety was achieved using microwave irradiation as well as thermal conditions. Reaction of 2-(1-(10H-phenothiazin-2-yl)ethylidene)hydrazine-1-carbothioamide with various types of hydrazonoyl halide or α-haloketone afforded corresponding thiazolyl phenothiazines in good to excellent yield. Mass, 1H and 13C nuclear magnetic resonance (NMR), ultraviolet–visible (UV–Vis), X-ray diffraction (XRD), and elemental analyses confirmed the structure of all the new derivatives. The reaction progressed under microwave irradiation in shorter reaction time with higher yield compared with the conventional method. The antimicrobial and antitumor activities of selected derivatives were investigated, revealing that some of them showed high potency compared with standard references.

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Acknowledgements

This work was supported by King Abdulaziz City for Science and Technology, Riyadh, Saudi Arabia (grant no. 37-1683 for postgraduate students).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, Saudi Arabia

    Manal M. Alsharekh, Ismail I. Althagafi & Mohamed R. Shaaban

  2. Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt

    Mohamed R. Shaaban & Thoraya A. Farghaly

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  1. Manal M. Alsharekh
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  2. Ismail I. Althagafi
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  3. Mohamed R. Shaaban
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  4. Thoraya A. Farghaly
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Correspondence to Thoraya A. Farghaly.

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Alsharekh, M.M., Althagafi, I.I., Shaaban, M.R. et al. Microwave-assisted and thermal synthesis of nanosized thiazolyl-phenothiazine derivatives and their biological activities. Res Chem Intermed 45, 127–154 (2019). https://doi.org/10.1007/s11164-018-3594-7

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