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Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and screening of their anticancer activity

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Abstract

Stereoselective synthesis of (Z)-methyl 2-[(Z)-3-substituted 2-[2-(2,4-dinitrophenyl)hydrazono]-4-oxothiazolidine-5-ylidene]acetates and (Z)-methyl 2-[(Z)-3-substituted 2-[2-(tosylhydrazono)-4-oxothiazolidine-5-ylidene]acetates via the cyclization of N-substituted 2-arylhydrazino-carbothioamides with dialkyl acetylenedicarboxylates in absolute ethanol is reported. The structures were confirmed by spectroscopic data as well as single-crystal X-ray analyses. The mechanism of nucleophilic addition and the role of electronic factors were discussed. The anticancer activity of the newly synthesized compounds was evaluated against a panel of 60 cell lines derived from 9 different types of cancers including, leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers and the results revealed that the cyclohexyl derivative has a significant broad anticancer activity, especially against different leukemia and colon cancer cell lines.

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Acknowledgements

The authors thank the Science and Technology Development Fund, STDF, Egypt for its financial supporting of Grant No. 22934. Prof Alaa A. Hassan is indebted to the AvH-Foundation for the donation of a Shimadzu 408 IR instrument.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Minia University, El Minia, 61519, Egypt

    Alaa A. Hassan, Ashraf A. Aly, Nasr K. Mohamed & Hendawy N. Tawfeek

  2. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Assiut, 71524, Egypt

    Mohamed Ramadan

  3. Institute of Organic Chemistry, Karlsruhe Institute of Technology, 76131, Karlsruhe, Germany

    Stefan Bräse

  4. Institute of Biological and Chemical Systems (IBCS-FMS), Karlsruhe Institute of Technology, Eggenstein-Leopoldshafen, Germany

    Stefan Bräse

  5. Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio I), 00014 University of Helsinki, Helsinki, Finland

    Martin Nieger

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  1. Alaa A. Hassan
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Correspondence to Alaa A. Hassan.

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Hassan, A.A., Aly, A.A., Ramadan, M. et al. Stereoselective synthesis of 2-(2,4-dinitrophenyl)hydrazono- and (2-tosylhydrazono)-4-oxo-thiazolidine derivatives and screening of their anticancer activity. Monatsh Chem 151, 1453–1466 (2020). https://doi.org/10.1007/s00706-020-02671-w

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  • DOI: https://doi.org/10.1007/s00706-020-02671-w

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