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One-Pot Multicomponent Synthesis and Anticancer Activity of 1,3-Cyclopentathiazine and Pyrimidothiazine Derivatives

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Abstract

Novel 1,3-cyclopentathiazine and pyrimidothiazine derivatives were synthesized starting from 7-benzyl-4-phenylcyclopenta[d][1,3]thiazin-2-amine (CTA) prepared by a one-pot multicomponent reaction of cyclopentanone, benzaldehyde, and thiourea. Cyclocondensation of CTA with benzylidenemalononitrile gave a pyrimidothiazine. Oxidation of cyclopentathiazine with hydrogen peroxide afforded the corresponding epoxide, while its alkylation with ethyl iodide yielded an N-ethyl derivative. Cyclopentylidenemalononitrile was reacted with formaline and carbon disulfide to obtain pyridine-4-carbonitrile and thiapyrane, respectively, and the reactions of cyclopentylidenemalononitrile with aryl isocyanate and aryl isothiocyanate gave condensed diimino-substituted cyclopentanaphthyridine-1,6-dione and dithiaacenaphthylene-3,8-diylidedibenzamide, respectively. Heating cyclopentanone with benzoyl isothiocyanate and benzoyl chloride produced a sulfide derivative and an enolic dione, respectively. The structures of the newly synthesized compounds were confirmed by spectral analysis, and some products were screened for anticancer activity.

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ACKNOWLEDGMENTS

The authors are grateful to Dr. Zainab Fathy Elsawah, Pharmacology Department, Faculty of Science, Zagazig University for performing and interpreting the biological activity testing results. The authors are also grateful to all associated personnel in any reference, who contributed in the present research.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Islamic University in Al-Madinah Al-Monawara, 42351, Al-Madinah Al-Monawara, Saudi Arabia

    R. A. Haggam

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

    R. A. Haggam, H. Y. Moustafa, M. G. Assy & H. M. Abd El-Rahman

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  1. R. A. Haggam
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  2. H. Y. Moustafa
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  3. M. G. Assy
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  4. H. M. Abd El-Rahman
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Correspondence to R. A. Haggam.

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Haggam, R.A., Moustafa, H.Y., Assy, M.G. et al. One-Pot Multicomponent Synthesis and Anticancer Activity of 1,3-Cyclopentathiazine and Pyrimidothiazine Derivatives. Russ J Org Chem 56, 916–923 (2020). https://doi.org/10.1134/S1070428020050279

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