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Synthesis, properties, and application of 4-nitrosemicarbazones

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Abstract

The studies of the condensation of 4-nitrosemicarbazide (4-NSC) with various aldehydes and ketones resulted in the development of an approach to the synthesis of N-nitrosemicarbazones, promising high-energy and biologically active compounds. Subsequent treatment with amines and alkalis led to the synthesis of water-soluble salts of nitrosemicarbazones, as well as the corresponding semicarbazones. The reaction of N,N′-diisopropyl- or N,N′-di-tert-butyl-1,2-ethanediimine with 4-nitrosemicarbazide led to the synthesis of glyoxal bis(nitrosemicarbazone) derivatives. A computer-aided screening using the PASS software showed a probability of high biological activity for the compounds obtained, whereas antiarrhythmic properties of camphor nitrosemicarbazone potassium salt were confirmed in experiments in rats.

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References

  1. S. G. Il´yasov, G. V. Sakovich, A. A. Lobanova, Propellants, Explos., Pyrotech., 2013, 38, 327.

    Article  Google Scholar 

  2. S. G. Il´yasov, A. A. Lobanova, N. I. Popov, I. V. Kazantsev, V. L. Varand, S. V. Larionov, Russ. J. Gen. Chem. (Engl. Transl.), 2006, 76, 1719 [Zh. Obshch. Khim, 2006, 76, 1795].

    Article  Google Scholar 

  3. S. G. Il´yasov, I. V. Kazantsev, Polzunovskii vestn. [Polzunov Bull.], 2013, No. 3, 28 (in Russian).

    Google Scholar 

  4. A. V. Pozdnyakov, V. S. Glukhacheva, S. G. Il´yasov, Polzunovskii vestn. [Polzunov Bull.], 2010, No. 4–1, 116 (in Russian).

    Google Scholar 

  5. V. S. Glukhacheva, S. G. Il´yasov, A. O. Bryzgalov, T. G. Tolstikova, Polzunovskii vestn. [Polzunov Bull.], 2013, No. 3, 140 (in Russian).

    Google Scholar 

  6. S. Malkondu, S. Erdemir, Tetrahedron, 2014, 70, 5494.

    Article  CAS  Google Scholar 

  7. A. C. L. Leite, D. R. de M. Moreira, L. C. D. Coelho, F. D. de Menezes, D. J. Brondani, Tetrahedron Lett., 2008, 49, 1538.

    Article  CAS  Google Scholar 

  8. P. Noblia, E. J. Baran, L. Otero, P. Draper, H. Cerecetto, M. González, O. E. Piro, E. E. Castellano, T. Inohara, Y. Adachi, H. Sakurai, D. Gambino, Eur. J. Inorg. Chem., 2004, 322.

    Google Scholar 

  9. R. Cao, A. Garcia, E. Castell, Monatsh. Chem., 1992, 123, 487.

    Article  CAS  Google Scholar 

  10. K. N. Zelenin, Sorosovskii obrazovat. zhurn. [Soros Educ. J.], 1996, 12, 41 (in Russian).

    Google Scholar 

  11. Database of Chemical Compounds and Mixtures PubChem.; http://pubchem.ncbi.nlm.nih.gov/compound/21122329. Date of request 04.09.2015.

  12. Database of Chemical Compounds and Mixtures PubChem.; http://pubchem.ncbi.nlm.nih.gov/compound/91622086. Date of request 04.09.2015.

  13. Yu. P. Kitaev, Gidrazony [Hydrazones], Nauka, Leningrad, 1974, 412 pp. (in Russian).

    Google Scholar 

  14. R. R. Gallucci, J. Chem. Eng. Data, 1982, 27, 217.

    Article  CAS  Google Scholar 

  15. C. M. Sabate, H. Delalu, Z. Allg. Chem., 2012, 638, 57.

    Article  Google Scholar 

  16. V. M. Kolb, J. W. Stupar, T. E. Janota, W. L. Duax, J. Org. Chem., 1989, 54, 2341.

    Article  CAS  Google Scholar 

  17. M. Pomerantz, S. Bittner, S. B. Khader, J. Org. Chem., 1982, 47, 2217.

    Article  CAS  Google Scholar 

  18. S. G. Il´yasov, V. S. Glukhacheva, Polzunovskii vestn. [Polzunov Bull.], 2006, No. 2–2, 68 (in Russian).

    Google Scholar 

  19. V. S. Glukhacheva, S. G. Il´yasov, Polzunovskii vestn. [Polzunov Bull.], 2014, No. 3, 8 (in Russian).

    Google Scholar 

  20. S. G. Il´yasov, M. V. Chikina, Tetrahedron Lett., 2013, 54, 1931.

    Article  Google Scholar 

  21. GOST (State Standard) 4545-88, Veshchestva vzryvchatye brizantnye. Metody opredeleniya kharakteristik chuvstvitel´nosti k udaru [Blasting Explosives. Methods for Determination of Sensitivity Characteristics to Impact], Publ. Standartov, Moscow, 1988, 15 pp. (in Russian).

    Google Scholar 

  22. GOST (State Standard) P 50835-95, Veshchestva vzryvchatye brizantnye. Metody opredeleniya kharakteristik chuvstvitel´nosti k treniyu pri udarnom sdvige [Blasting Explosives. Methods for Determination of Sensitivity Characteristics to Friction Caused by a Pressure Shock], Publ. Standartov, Moscow, 1996, 13 pp. (in Russian).

    Google Scholar 

  23. D. A. Filimonov, A. A. Lagunin, T. A. Gloriozova, A. V. Rudik, D. S. Druzhilovskii, P. V. Pogodin, V. V. Poroikov, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 444 [Khim. Geterotsikl. Soedin., 2014, 483].

    Article  CAS  Google Scholar 

  24. E. A. Dikusar, V. I. Potkin, N. G. Kozlov, R. T. Tlegenov, Khimiya rast. syr´ya [Chem. Plant Raw Materials], 2013, No. 1, 83 (in Russian).

    Google Scholar 

  25. S. G. Il´yasov, A. A. Lobanova, N. I. Popov, R. R. Sataev, Russ. J. Org. Chem. (Engl. Transl.), 2002, 38, 1731 [Zh. Org. Khim., 2002, 38, 1793].

    Article  Google Scholar 

  26. S. G. Il´yasov, E. O. Danilova, Propellants, Explos., Pyrotech., 2012, 37, 427.

    Article  Google Scholar 

  27. Federal Law No. 61-FZ from 12.04.2010 "Ob obrashchenii lekarstvennykh sredstv" ["On Circulation of Medicines"]; http:/www.fas.gov.ru/legislative-acts/legislative-acts_51259.html (in Russian).

  28. R. U. Khabriev, Rukovodstvo po eksperimental´nomu (doklinicheskomu) izucheniyu novykh farmakologicheskikh veshchestv [Manual on Experimental (Preclinical) Study of New Pharmacological Substances], Meditsina, Moscow, 2005, 832 pp. (in Russian).

    Google Scholar 

  29. Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv [Manual on Conducting Preclinical Studies of Medicines], Eds A. N. Mironov, V. A. Merkulov, N. D. Bunatyan, V. P. Bondarev, I. V. Borisevich, M. V. Zhuravlev, A. A. Movsesyants, N. V. Medunitsyn, M. A. Gorbunov, M. V. Supotnitskii, Grif and K, Moscow, 2012, 944 pp. (in Russian).

  30. L. N. Sernov, V. V. Gatsura, Elementy eksperimental’noi farmakologii [Elements of Experimental Pharmacology], Meditsina, Moscow, 2000, 352 pp. (in Russian).

    Google Scholar 

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Authors and Affiliations

  1. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, 1 ul. Sotsialisticheskaya, 659322, Biisk Altaiskogo Kraya, Russian Federation

    V. S. Glukhacheva, S. G. Il’yasov & G. V. Sakovich

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    T. G. Tolstikova, A. O. Bryzgalov & N. V. Pleshkova

Authors
  1. V. S. Glukhacheva
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  2. S. G. Il’yasov
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  3. G. V. Sakovich
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  4. T. G. Tolstikova
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  5. A. O. Bryzgalov
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  6. N. V. Pleshkova
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Correspondence to S. G. Il’yasov.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0550—0560, February, 2016.

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Glukhacheva, V.S., Il’yasov, S.G., Sakovich, G.V. et al. Synthesis, properties, and application of 4-nitrosemicarbazones. Russ Chem Bull 65, 550–560 (2016). https://doi.org/10.1007/s11172-016-1336-9

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  • DOI: https://doi.org/10.1007/s11172-016-1336-9

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