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Synthesis of New Thieno[2,3-d]pyrimidines Containing a 1,2,3-Triazole Ring and Their Therapeutic Response in NCI-60 Cell Line Panel

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Abstract

A series of new tetrahydro[1]benzothieno[2,3-d]pyrimidines containing a 1,2,3-triazole fragment linked through an oxymethylene spacer have been synthesized by click reaction of 4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidines with various aryl and alkyl azides in the presence of copper sulfate and sodium ascorbate as a catalyst. The structures of the synthesized compounds were characterized by various spectroscopic techniques (1H and 13C NMR, FT-IR, and mass spectrometry), and their in vitro anticancer activity against NCI-60 human tumor cell lines was evaluated. Among the compounds tested, N-(pyridine-3-yl)­acetamide derivative exhibited significant activity against several cancer cell lines, including SF-539 (CNS cancer), HCT-116 (colon cancer), OVCAR-8 (ovarian cancer), PC-3 (prostate cancer), and CCRF-CEM (leukemia).

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ACKNOWLEDGMENTS

The authors thank the Department of Chemistry, Saurashtra University, Rajkot, for providing laboratory facilities and Centre of Excellence (CoE), NFDD complex, Rajkot, for performing spectral analyses. The authors also thank the National Cancer Institute (National Institutes of Health, USA) for providing anticancer screening of the synthesized compounds.

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  1. Department of Chemistry, Saurashtra University, 360005, Rajkot, Gujarat, India

    K. A. Bhensdadia, N. H. Lalavani & S. H. Baluja

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  1. K. A. Bhensdadia
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Correspondence to S. H. Baluja.

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Bhensdadia, K.A., Lalavani, N.H. & Baluja, S.H. Synthesis of New Thieno[2,3-d]pyrimidines Containing a 1,2,3-Triazole Ring and Their Therapeutic Response in NCI-60 Cell Line Panel. Russ J Org Chem 57, 1668–1677 (2021). https://doi.org/10.1134/S107042802110016X

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