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Synthesis and Anti-Proliferative Activity of New Acridinyl and Benzothiazolyl-Based Triazole Glycosides via Click Cycloaddition and Their Tetrazolyl Analogs

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Abstract

Novel acridine and benzothiazole substituted 1,2,3-triazole glycosides were synthesized by using Cu(I)-Catalyzed Azide-Alkyne Cycloaddition (CAAC) known as Click reaction. The reaction of the starting substituted alkyne derivatives with glycopyranosyl azides afforded the corresponding 1,2,3-triazole acetylated N-glycoside products under click reaction conditions. In addition, 1,2,3-triazole glycosides with linking spacers between the sugar moiety, and the triazole ring or between the benzothiazole and the triazole rings as isosteric analogs of the synthesized glycosyl triazoles were also prepared by click cycloaddition. Furthermore, new tetrazolyl glycosides attached to the benzothiazole ring system as analogs of triazole glycosides were synthesized. The desired products were examined against different tumor cells such as the human colon (HCT-116), human lung carcinoma (A549), hepatocellular carcinoma (HepG2) and breast (MCF-7) cancer cell lines utilizing MTT assay. Generally, most of the desired compounds showed excellent activities against all tumor cells. The results also, revealed that the highly active compounds are benzothiazolyl-based triazole glycosides.

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Authors and Affiliations

  1. Department of Photochemistry, National Research Centre, P.O. Box 12622, Cairo, Dokki, Egypt

    Hala E. M. Tolan, Hanan A. Soliman & Wael A. El-Sayed

  2. Applied Organic Chemistry Department, National Research Center, P.O. Box 12622, Cairo, Dokki, Egypt

    Mohamed A. A. Radwan

  3. Department of Chemistry, College of Science, Qassim University, 51452, Buraydah, Saudi Arabia

    Mohamed A. A. Radwan & Wael A. El-Sayed

  4. Department of Tanning Materials and Leather Technology, National Research Centre, Dokki, Giza, 12622, Egypt

    Hanem M. Awad

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Tolan, H.E., Radwan, M.A., Soliman, H.A. et al. Synthesis and Anti-Proliferative Activity of New Acridinyl and Benzothiazolyl-Based Triazole Glycosides via Click Cycloaddition and Their Tetrazolyl Analogs. Russ J Bioorg Chem 46, 1136–1147 (2020). https://doi.org/10.1134/S1068162020060345

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