Skip to main content
Log in

New Synthesis of Some Isoxazole Derivatives and Their Antioxidant Properties

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

Abstract

A series of substituted ethyl 5-phenyl-1,2-oxazole-3-carboxylates were synthesized in good to excellent yields in one step using hydroxylamine base and ethyl 2,4-dioxo-4-(4-R-phenyl)butanoates bearing both electron-donating and electron-withdrawing moieties on the benzene ring, and antioxidant properties of the products were investigated by the DPPH method. The proposed method is suitable for the large-scale production of isoxazole derivatives.

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.

Fig. 1.
Scheme

REFERENCES

  1. Kumbhare, R.M., Kosurkar, U.B., Ramaiah, M.J., Dad­mal, T.L., Pushpavalli, S.N.C.V.L., and Pal-Bhadra, M., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 5424. https://doi.org/10.1016/j.bmcl.2012.07.041

    Article  CAS  PubMed  Google Scholar 

  2. Azzali, E., Machado, D., Kaushik, A., Vacondio, F., Flisi, S., Cabassi, C.S., Lamichhane, G., Viveiros, M., Costantino, G., and Pieroni, M., J. Med. Chem., 2017, vol. 60, p. 7108. https://doi.org/10.1021/acs.jmedchem.7b00793

    Article  CAS  PubMed  Google Scholar 

  3. Pinho e Melo, T.M.V.D., Curr. Org. Chem., 2005, vol. 9, p. 925. https://doi.org/10.2174/1385272054368420

    Article  CAS  Google Scholar 

  4. Stern, E., Muccioli, G.G., Millet, R., Goossens, J.-F., Farce, A., Chavatte, P., Poupaert, J.H., Lambert, D.M., Depreux, P., and Hénichart, J.-P., J. Med. Chem., 2006, vol. 49, p. 70. https://doi.org/10.1021/jm050467q

    Article  CAS  PubMed  Google Scholar 

  5. Arya, G.C., Kaur, K., and Jaitak, V., Eur. J. Med. Chem., 2021, vol. 221, article ID 113511. https://doi.org/10.1016/j.ejmech.2021.113511

  6. 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., and Seibert, K., J. Med. Chem., 2000, vol. 43, p. 775. https://doi.org/10.1021/jm990577v

    Article  CAS  PubMed  Google Scholar 

  7. Proschak, E., Heitel, P., Kalinowsky, L., and Merk, D., J. Med. Chem., 2017, vol. 60, p. 5235. https://doi.org/10.1021/acs.jmedchem.6b01287

    Article  CAS  PubMed  Google Scholar 

  8. Sheng, S., Sheng, W., Hu, Q., Qu, H., and Cai, M., J. Heterocycl. Chem., 2014, vol. 51, p. 315. https://doi.org/10.1002/jhet.1673

    Article  CAS  Google Scholar 

  9. Chary, R.G., Reddy, G.R., Ganesh, Y.S.S., Prasad, K.V., Raghunadh, A., Krishna, T., Mukherjee, S., and Pal, M., Adv. Synth. Catal., 2014, vol. 356, p. 160. https://doi.org/10.1002/adsc.201300712

    Article  CAS  Google Scholar 

  10. Sowmya, D.V., Teja, G.L., Padmaja, A., Prasad, V.K., and Padmavathi, V., Eur. J. Med. Chem., 2018, vol. 143, p. 891. https://doi.org/10.1016/j.ejmech.2017.11.093

    Article  CAS  PubMed  Google Scholar 

  11. Chalyk, B.A., Sosedko, A.S., Volochnyuk, D.M., Tolmachev, A.A., Gavrilenko, K.S., Liashuk, O.S., and Grygorenko, O.O., Org. Biomol. Chem., 2018, vol. 16, p. 9152. https://doi.org/10.1039/C8OB02257G

    Article  CAS  PubMed  Google Scholar 

  12. Vadivelu, M., Sampath, S., Muthu, K., Karthikeyan, K., and Praveen, C., J. Org. Chem., 2019 vol. 84, p. 13636. https://doi.org/10.1021/acs.joc.9b01896

    Article  CAS  PubMed  Google Scholar 

  13. Smirnov, A.Yu., Zaitseva, E.R., Belozerova, O.A., Alekseyev, R.S., Baleeva, N.S., Zagudaylova, M.B., Mikhaylov, A.A., and Baranov, M.S., J. Org. Chem., 2019, vol. 84, p. 15417. https://doi.org/10.1021/acs.joc.9b02427

    Article  CAS  PubMed  Google Scholar 

  14. Praveen, C., Kalyanasundaram, A., and Perumal, P.T., Synlett, 2010, vol. 2010, no. 5, p. 777. https://doi.org/10.1055/s-0029-1219342

    Article  CAS  Google Scholar 

  15. Hou, Y., Lu, S., and Liu, G., J. Org. Chem., 2013, vol. 78, p. 8386. https://doi.org/10.1021/jo401077q

    Article  CAS  PubMed  Google Scholar 

  16. Hou, X., Zhang, H., Chen, B.-C., Guo, Z., Singh, A., Goswami, A., Gilmore, J.L., Sheppeck, J.E., Dyck­man, A.J., Carter, P.H., and Mathur, A., Org. Process Res. Dev., 2017, vol. 21, p. 200. https://doi.org/10.1021/acs.oprd.6b00366

    Article  CAS  Google Scholar 

  17. Potkin, V.I., Petkevich, S.K., and Kurman, P.V., Russ. J. Org. Chem., 2011, vol. 48, p. 928. https://doi.org/10.1134/S1070428011060169

    Article  CAS  Google Scholar 

  18. Uludag, N. and Mutlu, H., Russ. J. Org. Chem., 2022, vol. 58, p. 1267. https://doi.org/10.1134/S1070428022090111

    Article  CAS  Google Scholar 

  19. Uludag, N., Russ. J. Org. Chem., 2020, vol. 56, p. 1640. https://doi.org/10.1134/S1070428020090225

    Article  CAS  Google Scholar 

  20. Patir, S. and Uludag, N., Tetrahedron, 2009, vol. 65, p. 115. https://doi.org/10.1016/j.tet.2008.10.102

    Article  CAS  Google Scholar 

  21. Bratanovici, B.-I., Nicolescu, A., Shova, S., Das­călu, I.-A., Ardeleanu, R., Lozan, V., and Roman, G., Res. Chem. Intermed., 2020, vol. 46, p. 1587. https://doi.org/10.1007/s11164-019-04052-3

    Article  CAS  Google Scholar 

  22. Akbarzadeh, T., Rafinejad, A., Mollaghasem, J.M., Safavi, M., Fallah-Tafti, A., Pordeli, M., Ardestani, S.K., Shafiee, A., and Foroumadi, A., Arch. Pharm., 2012, vol. 345, p. 386. https://doi.org/10.1002/ardp.201100345

    Article  CAS  Google Scholar 

  23. Vadivelu, M., Sampath, S., Muthu, K., Karthikeyan, K., and Praveen, C., Adv. Synth. Catal., 2021, vol. 363, p. 4941. https://doi.org/10.1002/adsc.202100730

    Article  CAS  Google Scholar 

  24. Ma, Y., Chen, Y., Lou, C., and Li, Z., Asian J. Org. Chem., 2020, vol. 9, p. 1018. https://doi.org/10.1002/ajoc.202000153

    Article  CAS  Google Scholar 

  25. Serdaroğlu, G., Uludag, N., Sugumar, P., and Raj­kumar, P., J. Mol. Struct., 2021, vol. 1244, article ID 130978. https://doi.org/10.1016/j.molstruc.2021.130978

  26. Kadere, S.B. and Sing, R.P., J. Food Sci. Technol., 2011, vol. 48, p. 412. https://doi.org/10.1007/s13197-011-0251-1

    Article  CAS  Google Scholar 

  27. Pérez, J.M. and Ramón, D.J., ACS Sustainable Chem. Eng., 2015, vol. 3, p. 2343. https://doi.org/10.1021/acssuschemeng.5b00689

    Article  CAS  Google Scholar 

  28. Barrett, A.G.M., Procopiou, P.A., and Voigtmann, U., Org. Lett., 2001, p. 3165. https://doi.org/10.1021/ol016479x

  29. Grob, J.E., Nunez, J., Dechantsreiter, M.A., and Hamman, L.G., J. Org. Chem., 2011, vol. 76, p. 10241. https://doi.org/10.1021/jo201973t

    Article  CAS  PubMed  Google Scholar 

  30. Andrzejak, V., Muccioli, G.G., Body-Malapel, M., El Bakali, J., Djouina, M., Renault, N., Chavatte, P., Desreumaux, P., Lambert, D.M., and Millet, R., Bioorg. Med. Chem., 2011, vol. 19, p. 3777. https://doi.org/10.1016/j.bmc.2011.04.057

    Article  CAS  PubMed  Google Scholar 

  31. Johansson, N.G., Turku, A., Vidilaseris, K., Dreano, L., Khattab, A., Pérez, D.A., Wilkinson, A., Zhang, Y., Tamminen, M., Grazhdankin, E., Kiriazis, A., Fish­wick, C.W.G., Meri, S., Yli-Kauhaluoma, J., Gold­man, A., Boije af Gennäs, G., and Xhaard, H., ACS Med. Chem. Lett., 2020, vol. 11, p. 605. https://doi.org/10.1021/acsmedchemlett.9b00537

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Funding

The study was financially supported by the Scientific and Technological Research Council of Turkey (TUBITAK project no. 112T503).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. Uludag.

Ethics declarations

The author declares that he has no conflicts of interest.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Uludag, N. New Synthesis of Some Isoxazole Derivatives and Their Antioxidant Properties. Russ J Org Chem 60, 490–494 (2024). https://doi.org/10.1134/S1070428024030175

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428024030175

Keywords:

Navigation