Skip to main content
Log in

Synthesis of novel isoxazole derivatives bearing kojic acid moiety and evaluation of their antimicrobial activity

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A novel series of 3,5-disubstituted isoxazoles bearing kojic acid moiety were synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of terminal alkynes with nitrile oxide formed in situ from the corresponding hydroximoyl chloride. Structures of the synthesized compounds were characterized using spectroscopic analysis data. Antimicrobial activity of the isoxazole conjugates was determined as MIC values by broth microdilution method against different bacteria: Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Salmonella typhi, and fungi Candida kefyr. The obtained results revealed notable antibacterial and antifungal activities of the compounds.

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.

Similar content being viewed by others

References

  1. Baraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D. Synthesis 1987, 857.

  2. Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel, B. S.; Seibert, K. J. Med. Chem. 2000, 43, 775.

    Article  CAS  Google Scholar 

  3. Magar, B. K.; Bhosale, V. N.; Berad, B. N. Chem. Sin. 2011, 2, 147.

    CAS  Google Scholar 

  4. Basha, S. S.; Divya, K.; Padmaja, A.; Padmavathi, V. Res. Chem. Intermed. 2015, 41, 10067.

    Article  CAS  Google Scholar 

  5. Kapoor, A.; Beniwal, R. Pharm. Lett. 2016, 8, 127.

    CAS  Google Scholar 

  6. Kankala, S.; Kankala, R. K.; Gundepaka, P.; Thota, N.; Nerella, S.; Gangula, M. R.; Guguloth, H.; Kagga, M.; Vadde, R.; Vasam, C. S. Bioorg. Med. Chem. Let. 2013, 23, 1306.

    Article  CAS  Google Scholar 

  7. Rajanarendar, E.; Rama Krishna, S.; Nagaraju, D.; Govardhan Reddy, K.; Kishore, B.; Reddy, Y. N. Bioorg. Med. Chem. Lett. 2015, 25, 1630.

    Article  CAS  Google Scholar 

  8. Hirpara, K.; Patel, S.; Joshi, A.; Parekh, H. Indian J. Heterocycl. Chem. 2004, 13, 221.

    CAS  Google Scholar 

  9. Tzanetou, E.; Liekens, S.; Kasiotis, K. M.; Melagraki, G.; Afantitis, A.; Fokialakis, N.; Haroutounian, S. A. Eur. J. Med. Chem. 2014, 81, 139.

    Article  CAS  Google Scholar 

  10. Garg, H. G.; Singh, P. P. J. Med. Chem. 1970, 13, 1250.

    Article  CAS  Google Scholar 

  11. Heasley, B. Angew. Chem., Int. Ed. 2011, 50, 8474.

  12. Bode, J. W.; Carreira, E. M. Org. Lett. 2001, 3, 1587.

    Article  CAS  Google Scholar 

  13. Yashiro, A.; Nishida, Y.; Kobayashi, K.; Ohno, M. Synlett 2000, 361.

  14. Müller, I.; Jäger, V. Tetrahedron Lett. 1982, 23, 4777.

    Article  Google Scholar 

  15. Lee, S. Y.; Lee, B. S.; Lee, C.-W.; Oh, D. Y. J. Org. Chem. 2000, 65, 256.

    Article  CAS  Google Scholar 

  16. Grünanger, P.; Vita-Finzi, P. In Chemistry of Heterocyclic Compounds: Isoxazoles; Wiley Interscience: New York, 1991, Vol. 49, p. 1.

  17. Nitta, M.; Kobayshi, T. J. Chem. Soc., Chem. Commun. 1982, 15, 877.

  18. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications; Wiley-VCH: Weinheim, 2003, 2nd ed., p. 138.

  19. Cuadrado, P.; González-Nogal, A. M.; Valero, R. Tetrahedron 2002, 58, 4975.

    Article  CAS  Google Scholar 

  20. Pinho e Melo, T. M. V. D. Curr. Org. Chem. 2005, 9, 925.

  21. Bondarenko, O. B.; Zyk, N. V. Chem. Heterocycl. Compd. 2020, 56, 694. [Khim. Geterotsikl. Soedin. 2020, 56, 694.]

  22. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984, Vol. 1, p. 1.

  23. Xu, J.; Hamme, A. T. Synlett 2008, 919.

  24. Kozikowski, A. P.; Adamczyk, M. J. Org. Chem. 1983, 48, 366.

    Article  CAS  Google Scholar 

  25. Grundmann, C.; Richter, R. J. Org. Chem. 1968, 33, 476.

    Article  CAS  Google Scholar 

  26. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.

    Article  CAS  Google Scholar 

  27. Yabuta, T. J. Chem. Soc., Trans. 1924, 125, 575.

  28. Mohamad, R.; Mohamed, M. S.; Suhaili, N.; Salleh, M. M.; Ariff, A. B. Biotechnol. Mol. Biol. Rev. 2010, 5, 24.

    CAS  Google Scholar 

  29. Mitani, H.; Koshiishi, I.; Sumita, T.; Imanari, T. Eur. J. Pharmacol. 2001, 411, 169.

    Article  CAS  Google Scholar 

  30. Higa, Y.; Kawabe, M.; Nabae, K.; Toda, Y.; Kitamoto, S.; Hara, T.; Tanaka, N.; Kariya, K.; Takahashi, M. J. Toxicol. Sci. 2007, 32, 143.

    Article  CAS  Google Scholar 

  31. Aytemir, M. D.; Özçelik, B. Eur. J. Med. Chem. 2010, 45, 4089.

    Article  CAS  Google Scholar 

  32. Sansho Seiyaku Co. JP Patent 80154916.

  33. Uher, M.; Konečný, V.; Rajniaková, O. Chem. Pap. 1994, 48, 282.

    CAS  Google Scholar 

  34. Khoeiniha, R.; Olyaei, A.; Saraei, M. J. Heterocycl. Chem. 2017, 54, 1746.

    Article  CAS  Google Scholar 

  35. Saraei, M.; Eftekhari-Sis, B.; Faramarzi, M.; Hossienzadeh, R. J. Heterocycl. Chem. 2014, 51, 1500.

    Article  CAS  Google Scholar 

  36. Masateru, M.; Shone, R. L. US Patent 4705871A.

  37. Williams, H. W. R. Can. J. Chem. 1976, 54, 3377.

    Article  CAS  Google Scholar 

  38. Bransová, J.; Uher, M.; Brtko, J. Chem. Pap. 1993, 47, 316.

    Google Scholar 

  39. Tehrani, M. B.; Emani, P.; Rezaei, Z.; Khoshneviszadeh, M.; Ebrahimi, M.; Edraki, N.; Mahdavi, M.; Larijani, B.; Ranjbar, S.; Foroumadi, A.; Khoshneviszadeh, M. J. Mol. Struct. 2019, 1176, 86.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mahnaz Saraei.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 823–827

Supplementary Information

ESM 1

(PDF 5135 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khodabandlou, S., Saraei, M. Synthesis of novel isoxazole derivatives bearing kojic acid moiety and evaluation of their antimicrobial activity. Chem Heterocycl Comp 57, 823–827 (2021). https://doi.org/10.1007/s10593-021-02986-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02986-4

Keywords

Navigation