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Glycylglycine and Its Morpholide Derivatives Containing 5-(p-Tolyl)isoxazole and 4,5-Dichloroisothiazole Moieties

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Abstract

The acylation of glycylglycine and its morpholide with 4,5-dichloroisothiazole-3-carbonyl chloride gave the corresponding N-(4,5-dichloroisothiazole-3-ylcarbonyl) derivatives. N-[5-(p-Tolyl)isoxazole-3-car­bonyl] analogs were synthesized by acylation of glycylglycine and its morpholide with 5-(p-tolyl)isoxazole-3-carbonyl azide since treatment of the same substrates with 5-(p-tolyl)isoxazole-3-carbonyl resulted in the formation of mixtures of products. The reactions of glycylglycine and its morpholide with phenyl N-(4,5-di­chloroisothiazol-3-yl)- and N-[(p-tolyl)isoxazol-3-yl]carbamates afforded derivatives containing an urea fragment. Some of the synthesized compounds showed antitumor activity and enhanced the antitumor effect of doxorubicin.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 220072, Minsk, Belarus

    I. A. Kolesnik, A. V. Kletskov, V. I. Potkin, V. A. Knizhnikov & T. D. Zvereva

  2. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141, Minsk, Belarus

    P. V. Kurman

  3. Institute of Physiology, National Academy of Sciences of Belarus, 220072, Minsk, Belarus

    Yu. P. Tokalchik & V. A. Kulchitsky

Authors
  1. I. A. Kolesnik
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  2. A. V. Kletskov
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  3. V. I. Potkin
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  4. V. A. Knizhnikov
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  5. T. D. Zvereva
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  6. P. V. Kurman
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  7. Yu. P. Tokalchik
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  8. V. A. Kulchitsky
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Correspondence to I. A. Kolesnik.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1382–1392 https://doi.org/10.31857/S0514749221100037.

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Kolesnik, I.A., Kletskov, A.V., Potkin, V.I. et al. Glycylglycine and Its Morpholide Derivatives Containing 5-(p-Tolyl)isoxazole and 4,5-Dichloroisothiazole Moieties. Russ J Org Chem 57, 1584–1591 (2021). https://doi.org/10.1134/S1070428021100031

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  • DOI: https://doi.org/10.1134/S1070428021100031

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