Skip to main content
Log in

Synthesis, Structure, and Biological Activity of N-p-(Dimethylamino)-N′-(p-dimethylaminobenzylidene)-N,N′′-diphenylbenzohydrazonohydrazide

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A three-component reaction of 3,5-diacetyl-2,6-dimethylpyridine, p-N-dimethylaminobenzaldehyde and phenylhydrazine in the presence of KOH in ethanol gave the condensation product of two p-N-dimethylaminobenzaldehyde and phenylhydrazine molecules, namely bis(biarylhydrazone). Structure of the obtained derivative was proved by the 1H and 13C NMR spectroscopy and X-ray diffraction analysis data. It was shown that the bis(biarylhydrazone) derivative has high antiradical and cytoprotective activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Fig. 1.
Scheme

Similar content being viewed by others

REFERENCES

  1. Palecek, J., Vondra, K., and Kuthan, J., Collect. Czech. Chem. Commun., 1969, vol. 34, p. 2991.

    Article  CAS  Google Scholar 

  2. Kulakov, I.V., Karbainova, A.A., Shulgau, Z.T., Seilkhanov, T.M., Gatilov, Y.V., and Fisyuk, A.S., Chem. Heterocycl. Compd., 2017, vol. 53, no. 10, p. 1094. https://doi.org/10.1007/s10593-017-2178-6

    Article  CAS  Google Scholar 

  3. Pi, Y., Wang, D.-J., Liu, H., Hu, Y.-J., Wei, X.-H., and Zheng, J., Spectrochim. Acta (A), 2014, vol. 131, p. 209. https://doi.org/10.1016/j.saa.2014.04.078

    Article  CAS  Google Scholar 

  4. Kozmik, V., Lhotak, P., Odlerova, Z., Palecek, J., Collect. Czech. Chem. Commun., 1998, vol. 63, no. 5, p. 698. https://doi.org/10.1135/cccc19980698

    Article  CAS  Google Scholar 

  5. Lhotak, P. and Kurfuerst, A., Collect. Czech. Chem. Commun., 1992, vol. 57, no. 9, p. 1937. https://doi.org/10.1135/cccc19921937

    Article  CAS  Google Scholar 

  6. Desenko, S.M. and Orlov, V.D., Azageterotsikly na osnove aromaticheskikh nepredel’nykh ketonov (Azaheterocycles Based on Aromatic Unsaturated Ketones), Kharkov: Folio, 1998.

  7. Chebanov, V.A., Desenko, S.M., and Gurley, T.W., Azaheterocycles Based on α,β-Unsaturated Carbonyls, Berlin-Heidelberg: Springer-Verlag, 2008.

  8. Abdel-Latif, N.A., Sabry, N.M., Mohamed, A.M., and Abdulla, M.M., Monatsh. Chem., 2007, vol. 138, no. 7, p. 715. https://doi.org/10.1007/s00706-007-0656-8

    Article  CAS  Google Scholar 

  9. Stalinskaya, A.L., Weber, D.F., Seilkhanov, T.M., and Kulakov, I.V., Monatsh. Chem., 2021, vol. 152, no. 3, p. 337. https://doi.org/10.1007/s00706-021-02751-5

    Article  CAS  Google Scholar 

  10. Lone, I.H., Khan, K.Z., Fozdar, and Bharat, B.I., Med. Chem. Res., 2014, vol. 23, no. 1, p. 363. https://doi.org/10.1007/s00044-013-0643-z

    Article  CAS  Google Scholar 

  11. Sowmya, P.V., Poojary, B., Revanasiddappa, B.C., Vijayakumar, M., Nikil, P., and Kumar, V., Res. Chem. Intermed., 2017, vol. 43, no. 12, p. 7399. https://doi.org/10.1007/s11164-017-3083-4

    Article  CAS  Google Scholar 

  12. Zhang, J., Zhang, M., Cao, W., Song, L., Qian, Q., and Tan, J., Heteroatom Chem., 2009, vol. 20, no. 3, p. 123. https://doi.org/10.1002/hc.20522

    Article  CAS  Google Scholar 

  13. Oleshchuk, A.L., Karbainova, A.A., Krivoruchko, T.N., Shulgau, Z.T., Seilkhanov, T.M., and Kulakov, I.V., Chem. Heterocycl. Compd., 2019, vol. 55, no. 1, p. 47. https://doi.org/10.1007/s10593-019-02417-5

    Article  CAS  Google Scholar 

  14. Krasovickii, B.M. and Afanasiadi, L.M., Preparativnaya khimiya organicheskikh lyuminoforov (Preparative Chemistry of Organic Phosphors), Kharkov: Folio, 1997, p. 117.

  15. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc. Perkin Trans. 2, 1987, p. S1. https://doi.org/10.1039/p298700000s1

  16. Guru, M.M. and Punniyamurthy, T., J. Org. Chem., 2012, vol. 77, no. 11, p. 5063. https://doi.org/10.1021/jo300592t

    Article  CAS  PubMed  Google Scholar 

  17. Milligan, T.W. and Minor, B.C., J. Org. Chem., 1962, vol. 27, no. 12, p. 4663. https://doi.org/10.1021/jo01059a517

    Article  CAS  Google Scholar 

  18. Barton, D.H.R., Ducker, J.W., Lord, W.A., and Magnus, P.D., J. Chem. Soc. Perkin Trans. 1, 1976, vol. 1, p. 38. https://doi.org/10.1039/P19760000038

    Article  Google Scholar 

  19. Velikorodov, A.V., Russ. J. Org. Chem., 2004, vol. 40, no. 10, p. 1490. https://doi.org/10.1007/s11178-005-0047-8

    Article  CAS  Google Scholar 

  20. Buzykin, B.I. and Gazetdinova, N.G., Bull. Acad. Sci. USSR. Div. Chem. Sci., 1980, vol. 29, no. 7, p. 1159.

    Article  Google Scholar 

  21. Zhmurova, I.N. and Yurchenko, R.I., J. Gen. Chem., 1977, vol. 47, p. 927.

    Google Scholar 

  22. Woodward, R.B. and Wintner, C., Tetrahedron Lett., 1969, vol. 10, no. 32, p. 2697. https://doi.org/10.1016/S0040-4039(01)88246-0

    Article  Google Scholar 

  23. Hegarty, A.F., Kearney, J.A., and Scott F.L, J. Chem. Soc. Perkin Trans. 2, 1973, vol. 10, p. 1422. https://doi.org/10.1039/P29730001422

    Article  Google Scholar 

  24. Brand-Williams, W., Cuvelier, M.E., and Berset, C., Lebensm Wiss Technol., 1995, vol. 28, p. 25. https://doi.org/10.1016/S0023-6438(95)80008-5

    Article  CAS  Google Scholar 

  25. Sergazy Sh., Gulyayev, A., Amangeldiyeva, A., Nurgozhina, A., Nurgaziyev, M., Shulgau, Z., Chulenbayeva, L., Khassenbekova, Z., Kushugulova, A., and Aljofan, M., Front. Pharmacol., 2021, vol. 12, article 687763. https://doi.org/10.3389/fphar.2021.687763

  26. Bacanli, M., Anlar H.G, Basaran, A.A., and Basaran, N., Turk. J. Pharm. Sci., 2017, vol. 14, no. 2, p. 95. https://doi.org/10.4274/tjps.07078

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. CrysAlisPro, Yarnton, Oxfordshire, England: Agilent Technologies Ltd., 2014.

  28. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  29. Sheldrick, G.M., Acta Crystallogr. (C), 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

Spectrophotometric studies were carried out using the equipment of the Center for Collective Use “Rational Nature Management and Physical and Chemical Research” of the Tyumen State University.

Funding

The work was supported financially by the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan (grant “Determination of the cytoprotective potential of pharmacologically active compounds with previously established high antioxidant activity”, IRN AP09562310).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sh. D. Sergazy.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Stalinskaya, A.L., Shulgau, Z.T., Sergazy, S.D. et al. Synthesis, Structure, and Biological Activity of N-p-(Dimethylamino)-N′-(p-dimethylaminobenzylidene)-N,N′′-diphenylbenzohydrazonohydrazide. Russ J Gen Chem 92, 147–153 (2022). https://doi.org/10.1134/S1070363222020025

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363222020025

Keywords:

Navigation