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Synthesis and biological activity of 2-sulfonarylhydrazinylidene 1,3-diketones and their pyrazole derivatives

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Abstract

2-Sulfonarylhydrazinylidene 1,3-diketones were synthesized by the azo coupling of aryldiazonium salts containing a methylsulfonyl or sulfonamide moiety with trifluoromethyl-1,3-diketones or their lithium salts. The cyclization of the latter with hydrazine hydrate, 4-hydrazinylbenzenesulfonamide hydrochloride, and 4-nitrophenylhydrazine yielded a series of 4-sulfonaryldiazenylpyrazoles. Their transformations with 4-nitrophenylhydrazine were not selective. Cytotoxicity on A549, Hep-2, and HeLa cancer cell cultures, antiviral activity against A/Puerto Rico/8/34 (H1N1) influenza virus, analgesic activity in the “hot plate” test, and antimicrobial activity against pathogenic fungi (dermatophytes, yeast-like fungi of the Candida genus, and Neisseria gonorrhoeae bacteria) were studied for the synthesized compounds.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi, 620137, Ekaterinburg, Russian Federation

    O. G. Khudina, N. A. Elkina, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess & V. I. Saloutin

  2. St. Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 ul. Mira, 197101, St. Petersburg, Russian Federation

    Ya. L. Esaulkova & V. V. Zarubaev

  3. A. A. Smorodintsev Research Institute of Influenza, 15/17 ul. Professora Popova, 197376, St. Petersburg, Russian Federation

    A. A. Shtro

  4. Perm National Research Polytechnic University, 29 Komsomol’skii prosp., 614990, Perm, Russian Federation

    G. A. Triandafilova, O. P. Krasnykh & K. O. Malysheva

  5. Ural Research Institute of Dermatovenereology and Immunopathology, 8 ul. Shcherbakova, 620076, Ekaterinburg, Russian Federation

    N. A. Gerasimova & N. P. Evstigneeva

Authors
  1. O. G. Khudina
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  2. N. A. Elkina
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  3. Ya. V. Burgart
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  4. M. A. Ezhikova
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  14. V. I. Saloutin
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Corresponding author

Correspondence to V. I. Saloutin.

Additional information

Based on the materials of the V Russian Conference on Medicinal Chemistry with international participation “MedChem-Russia 2021” (May 16–19, 2022, Volgograd, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2670–2684, December, 2022.

This work was carried out in terms of the contract of the Ministry of Education and Science of the RF No. 075-15-2020-777 using the equipment of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds.”

The operation with laboratory animals was conducted by professional veterinarian, pharmacologist, and trained specialists. All procedures performed in the studies involving animals were in accord with legal acts of the RF and international organizations.37,38

The authors declare no competing interests.

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Khudina, O.G., Elkina, N.A., Burgart, Y.V. et al. Synthesis and biological activity of 2-sulfonarylhydrazinylidene 1,3-diketones and their pyrazole derivatives. Russ Chem Bull 71, 2670–2684 (2022). https://doi.org/10.1007/s11172-022-3696-7

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