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Russian Journal of General Chemistry

, Volume 89, Issue 7, pp 1519–1527 | Cite as

Aurones and Analogues: Promising Heterocyclic Scaffolds for Development of Antioxidant and Antimicrobial Agents

  • M. IrshadEmail author
  • Q. Ali
  • F. Iram
  • S. A. Ahamad
  • M. Saleem
  • M. Saadia
  • M. Batool
  • A. Kanwal
  • S. Tabassum
Article

Abstract

Synthesis of some new multi-functional analogues of 2′-hydroxy chalcone containing isoxazole and pyrazole functions were synthesized, and their pharmacological activity was tested. Chalcone derivatives were synthesized by the reaction of 2′-hydroxy acetophenone with various substituted benzaldehydes in a basic medium. Aurones were isolated upon treatment with mercuric acetate. Synthesized chalcones and aurones were converted into the corresponding isoxazole and pyrazole derivatives upon their reaction with hydroxylamine hydrochloride or hydrazine hydrate, respectively. Structures of the compounds were confirmed by spectroscopic methods. All synthesized compounds were tested for antioxidant and antibacterial potential. Some of those demonstrated excellent antioxidant activity, and one product was identified as a promising antimicrobial candidate.

Keywords

chalcones pyrazolic isoxazolic aurones 2′-hydroxyacetophenone antioxidant antimicrobial 

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References

  1. 1.
    Rahman, A., Qureshi, R., Kiran, M., and Ansari, F.L., Turk. J. Chem., 2007, vol. 31, p. 25.Google Scholar
  2. 2.
    Dubey, R.K., Dixit, P., and Arya, S., Int. J. Innov. Res. Sci., Eng. Technol., 2014, vol. 3, no. 1, p. 8141.Google Scholar
  3. 3.
    Haudecoeur, R. and Boumendjel, A., Curr. Med. Chem., 2012, vol. 19, p. 2861. doi  https://doi.org/10.2174/092986712800672085 CrossRefGoogle Scholar
  4. 4.
    Deepthi, M., Harinadha, B.V, and Madhava, R.B., Indian J. Chem., 2013, vol. 52, p. 1455.Google Scholar
  5. 5.
    Lee, C.Y., Chew, E.H., and Go, M.L., Eur. J. Med. Chem., 2010, vol. 45, no. 7, p. 2957. doi  https://doi.org/10.1016/j.ejmech.2010.03.023.CrossRefGoogle Scholar
  6. 6.
    Zheng, X., Wang H., Yun-Mei, L., Xu, Y., Min, T., Yu-Hong, W., and Duan-Fang, L., J. Heterocycl. Chem., 2015, vol. 52, p. 296. doi  https://doi.org/10.1002/jhet.1969 CrossRefGoogle Scholar
  7. 7.
    Carrasco, M.P., Newton, A.S., Goncalves, L., Gois, A., Machado, M., Gut, J., Nogueira, F., Hanscheid, T., Guedes, R.C., Santos, D.J.V.A., Rosenthal, P.J., and Moreira, R., Eur. J. Med. Chem., 2014, vol. 80, p. 523. doi  https://doi.org/10.1016/j.ejmech.2014.04.076.CrossRefGoogle Scholar
  8. 8.
    Bandgar, B.P. and Patil, S.A., Eur. J. Med. Chem., 2010, vol. 45, p. 3223. doi  https://doi.org/10.1016/j.ejmech.2010.03.045.CrossRefGoogle Scholar
  9. 9.
    Shin, S.Y., Shin, M.C., Shin, J.S., Lee, K.T., and Lee, Y.S. Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 4520. doi  https://doi.org/10.1016/j.bmcl.2011.05.117.CrossRefGoogle Scholar
  10. 10.
    Detsi, A., Majdalani, M., Kontogiorgis, C.A., Hadjipavlou-Litina, D., and Kefalas, P., Bioorg. Med. Chem., 2009, vol. 17, p. 8073. doi  https://doi.org/10.1016/j.bmc.2009.10.002 CrossRefGoogle Scholar
  11. 11.
    Zhuang, Y., Chen, L., Sun, L., and Cao, J., J. Funct. Foods, 2012, vol. 4, p. 331. doi  https://doi.org/10.1016/j.jff.2012.01.001 CrossRefGoogle Scholar
  12. 12.
    Oyaizu, M., Jpn. J. Nutr. Diet., 1986, vol. 44, p. 307. doi  https://doi.org/10.5264/eiyogakuzashi.44.307 CrossRefGoogle Scholar
  13. 13.
    Harrigan, F.W., Laboratory Methods in Food Microbiology, London: Academic Press, 1998, 3rd ed.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • M. Irshad
    • 1
    Email author
  • Q. Ali
    • 1
  • F. Iram
    • 2
  • S. A. Ahamad
    • 2
  • M. Saleem
    • 3
  • M. Saadia
    • 4
  • M. Batool
    • 5
  • A. Kanwal
    • 1
  • S. Tabassum
    • 1
  1. 1.Department of Chemistry, Division of Science and TechnologyUniversity of Education LahoreLahorePakistan
  2. 2.Department of ChemistryLahore College for Women UniversityLahorePakistan
  3. 3.Department of ChemistryUniversity of Education DG Khan CampusDera Ghazi KhanPakistan
  4. 4.Department of BiochemistryUniversity of SargodhaSargodhaPakistan
  5. 5.Department of ChemistryUniversity of PunjabLahorePakistan

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