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Russian Journal of General Chemistry

, Volume 89, Issue 7, pp 1360–1367 | Cite as

Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives

  • O. A. Nurkenov
  • M. K. IbraevEmail author
  • I. A. Schepetkin
  • A. I. Khlebnikov
  • T. M. Seilkhanov
  • A. E. Arinova
  • M. B. Isabaeva
Article

Abstract

Functionally substituted chalcones, pyrazolines, and flavonones have been synthesized. Their structure has been studied by means of 1H and 13C NMR spectroscopy, including COSY and HMQC experiments. Anti-inflammatory activity of the synthesized chalcones, pyrazolines, and flavonones has been evaluated.

Keywords

substituted aromatic aldehydes chalcone pyrazoline flavonone cytokine transcription factor NF-κB 

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Notes

Funding

This study was financially supported by the Ministry of Education and Science of the Russian Federation (project no. 4.6660.2017/8.9) and the Ministry of Education and Science of the Republic of Kazakhstan (project no. AP05133157).

References

  1. 1.
    Daskiewicz, J.B., Comte, G., Barron, D., Di Pietro, A., and Thomasson, F., Tetrahedron Lett., 1999, vol. 40, p. 7095. doi  https://doi.org/10.1016/S0040-4039(99)01461-6 CrossRefGoogle Scholar
  2. 2.
    Miranda, C.L., Aponso, G.L.M., Stevens, J.F., Deinzer, M.L., and Buhler, D.R., J. Agric. Food Chem., 2000, no. 48, p. 3876. doi  https://doi.org/10.1021/jf0002995
  3. 3.
    Sivakumar, P.M., Prabhakar, P.K., and Doble, M., Med. Chem. Res., 2011, vol. 20, no. 4, p. 482. doi  https://doi.org/10.1007/s00044-010-9342-1 CrossRefGoogle Scholar
  4. 4.
    Tiwari, K.N., Monserrat, J.P., Arnaud Hequet, A., Ganem-Elbaz, C., Cresteil, T., Jaouen, G., Vessières, A., Hillard, E.A., and Jolivalt, C., Dalton Trans., 2012, vol. 41, p. 6451. doi  https://doi.org/10.1039/C2DT12180H CrossRefGoogle Scholar
  5. 5.
    Dao, T.T., Nguyen, P.H., Lee, H.S., Kim, E., Park, J., Lim, S., and Oh, W.K., Bioorg. Med. Chem. Lett., 2011, vol. 21, no. 1, p. 294. doi  https://doi.org/10.1016/j.bmcl.2010.11.016 CrossRefGoogle Scholar
  6. 6.
    Hsieh, H.K., Tsao, L.T., and Wang, J.P., J. Pharm. Pharmacol., 2000, vol. 52, no. 2, p. 163. doi  https://doi.org/10.1211/0022357001773814 CrossRefGoogle Scholar
  7. 7.
    Awasthi, S.K., Mishra, N., Kumar, B., Sharma, M., Bhattacharya, A., Mishra, L.C., and Bhasin, VK., Med. Chem. Res., 2009, vol. 18, no. 6, p. 407. doi  https://doi.org/10.1007/s00044-008-9137-9 CrossRefGoogle Scholar
  8. 8.
    Achanta, G., Modzelewska, A., Feng, L., Khan, S.R., and Huang, P.A., Mol. Pharmacol., 2006, vol. 70, no. 1, p. 426. doi  https://doi.org/10.1124/mol.105.021311 CrossRefGoogle Scholar
  9. 9.
    Barford, L., Kemp, K., Hansen, M., and Kharazmi, A., Int. Immunopharmacol., 2002, vol. 2, p. 545. doi  https://doi.org/10.1016/S1567-5769(01)00202-8 CrossRefGoogle Scholar
  10. 10.
    Satyanarayama, M., Tiwari, P., Tripathi, K., Srivastava, A.K., and Pratap, R., Bioorg. Med. Chem., 2004, vol. 12, no. 5, p. 883. doi  https://doi.org/10.1016/j.bmc.2003.12.026 CrossRefGoogle Scholar
  11. 11.
    Hamdi, N., Fischmeister, C., Puerta, M.C., and Valerga, P., Med. Chem. Res., 2011, vol. 20, no. 4, p. 522. doi  https://doi.org/10.1007/s00044-010-9326-1 CrossRefGoogle Scholar
  12. 12.
    Lahtchev, K.L., Batovska, D.I., Parushev, S.P., Ubiyvovk, V.M., and Sibirny, A.A., Eur. J. Med. Chem., 2008, vol. 43, no. 10, p. 2220. doi  https://doi.org/10.1016/j.ejmech.2007.12.027 CrossRefGoogle Scholar
  13. 13.
    Takagi, K., Tanaka, M., Murakami, Y., Morita, H., and Aotsuka, T., Eur. J. Med. Chem. Chim. Ther., 1986, vol. 21, p. 65.Google Scholar
  14. 14.
    Ankhiwala, M.D. and Naik, H.B., J. Indian Chem. Soc., 1990, vol. 67, no. 3, p. 258; C. A., 1991, vol. 4, p. 816.Google Scholar
  15. 15.
    Kaname, T., Masaaki, T., Hikari, M., Kuniyoshi, O., Katsuyuki, I., Naoki, N., and Masayuki, O., Eur. J. Med. Chem., 1987, vol. 22, p. 239. doi  https://doi.org/10.1016/0223-5234(87)90055-9 CrossRefGoogle Scholar
  16. 16.
    Litvinenko, V.I., Prirodnye flavonoidy, (Natural Flavonoids), Kharkiv: GNTsLS 1995.Google Scholar
  17. 17.
    Aitmambetov, A. and Kubzheterova, A., Russ. J. Bioorg. Chem., 2002, vol. 28, p. 165. doi  https://doi.org/10.1023/A:1015081726977 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • O. A. Nurkenov
    • 1
    • 2
  • M. K. Ibraev
    • 1
    Email author
  • I. A. Schepetkin
    • 3
    • 4
  • A. I. Khlebnikov
    • 4
    • 5
  • T. M. Seilkhanov
    • 6
  • A. E. Arinova
    • 2
  • M. B. Isabaeva
    • 1
  1. 1.Karaganda State Technical UniversityKaragandaKazakhstan
  2. 2.Institute of Organic Synthesis and Coal Chemistry of the Republic of KazakhstanKaragandaKazakhstan
  3. 3.Department of Immunology and Infectious DiseasesMontana State UniversityBozemanUSA
  4. 4.N. Kizhner CenterNational Research Tomsk Polytechnic UniversityTomskRussia
  5. 5.I.I. Polzunov Altai State Technical UniversityBarnaulRussia
  6. 6.Sh. Ualikhanov Kokshetau State UniversityKokshetauKazakhstan

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