Skip to main content
SpringerLink
Log in

Synthesis and Antimicrobial and Analgesic Activity of Products of the Recyclization of 5-(Het)Aryl-4-(trifluoromethyl)furan-2,3-diones under the Action of Aromatic Amines

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

Abstract

4-Substituted 5-hydroxy-5-(trifluoromethyl)dihydrofuran-2,3-diones were synthesized by the reaction of 5-substituted 4,4,4-trifluoroacetylfuran-2,3-diones with aromatic amines. The synthesized compounds exhibited the antibacterial and antinociceptive activity.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Scheme
Fig. 2.

REFERENCES

  1. Nekrasov, D.D., Maslivets, A.N., Lisovenko, N.Yu., Zalesov, V.V., Pulina, N.A., and Rubtsov, A.E., Pyatichlennye geterotsikly s vitsinal’nymi dioksogruppami (Five-Membered Heterocycles with Vicinal Oxo Groups), Perm: Perm. Univ., 2004, p. 39.

  2. Andreichikov, Yu.S., Gein, V.L., Zalesov, V.V., Kozlov, A.P., Kolents, G., Maslivets, A.N., Pimenova, E.V., and Shurov, S.N., Khimiya pyatichlennykh 2,3-dioksogeterotsiklov (Chemistry of Five-Term 2,3-Dioxoheterocycles), Perm: Izd: Perm. Univ., 1994, p. 5.

  3. El’chishcheva, N.V. and Konovalova, V.V., Russ. J. Org. Chem., 2018, vol. 54, p. 664. https://doi.org/10.1134/S1070428018040279

    Article  Google Scholar 

  4. Ivanov, D.V., Igidov, N.M., and Rubtsov, A.E., Russ. J. Org. Chem., 2016, vol. 52, p. 676. https://doi.org/10.1134/S1070428016050109

    Article  CAS  Google Scholar 

  5. Pulina, N.A., Lipatnikov, K.V., and Sobin, F.V., Russ. J. Gen. Chem., 2018, vol. 88, p. 1618. https://doi.org/10.1134/S107036321808011X

    Article  CAS  Google Scholar 

  6. Fäseke, V.C. and Sparr, C., Angew. Chem., Int. Ed., 2016, vol. 55, p. 7261. https://doi.org/10.1002/anie.201602689

    Article  CAS  Google Scholar 

  7. Barbier, V., Couty, F., and David, O.R.P., Tetrahedron, 2016, vol. 72, p. 5646. https://doi.org/10.1016/j.tet.2016.07.072

    Article  CAS  Google Scholar 

  8. Kibriz, I.E., Saçmaci, M., Sahin, E., and Yildirim, I., Tetrahedron, 2017, vol. 73, p. 1795. https://doi.org/10.1016/j.tet.2017.01.046

    Article  CAS  Google Scholar 

  9. Lisovenko, N.Yu., Dryahlov, A.V., and Dmitriev, M.V., Russ. J. Org. Chem., 2016, vol. 52, p. 1183. https://doi.org/10.1134/S1070428016080157

    Article  CAS  Google Scholar 

  10. Elʼchishcheva, N.V., Dmitriev, M.V., and Konovalova, V.V., Russ. J. Org. Chem., 2020, vol. 56, p. 400. https://doi.org/10.1134/S1070428020030069

    Article  Google Scholar 

  11. Stepanova, E.E., Dmitriev, M.D., and Maslivets, A.N., Beilstein J. Org. Chem., 2020, vol. 16, p. 2322. https://doi.org/10.3762/bjoc.16.193

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Panchenko, A.O., Shipilovskikh, S.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2016, vol. 52, p. 343. https://doi.org/10.1134/S107042801603009X

    Article  CAS  Google Scholar 

  13. Lakshmi, S., Rajan, P.R., Eringathodi, S., and Vijay, N., Synlett, 2014, vol. 25, p. 853. https://doi.org/10.1055/s-0033-1340715

    Article  CAS  Google Scholar 

  14. Wang, Z.-D., Wang, F., Li, X., and Cheng, J.-P., Org. Biomol. Chem., 2013, vol. 11, p. 5634. https://doi.org/10.1039/C3OB41028E

    Article  CAS  PubMed  Google Scholar 

  15. Wang, Z.-D., Dong, N., Wang, F., Li, X., and Cheng, J.-P., Tetrahedron Lett., 2013, vol. 54, p. 5473. https://doi.org/10.1016/j.tetlet.2013.07.129

    Article  CAS  Google Scholar 

  16. Masaaki, Y. and Yasunori, Y., Tetrahedron Asymmetry, 2015, vol. 26, p. 1430. https://doi.org/10.1016/j.tetasy.2015.10.010

    Article  CAS  Google Scholar 

  17. Üngoeren, S.H., Dilekoglu, E., and Koca, I., Chin. Chem. Lett., 2013, vol. 24, p. 1130. https://doi.org/10.1016/j.cclet.2013.08.001

    Article  CAS  Google Scholar 

  18. Khlebnikov, A.F., Novikov, M.S., Pakalnis, V.V., Iakovenko, R.O., and Yufit, D.S., Beilstein J. Org. Chem., 2014, vol. 10, p. 784. https://doi.org/10.3762/bjoc.10.74

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Bhunia, A., Roy, T., Gonnade, R.G., and Biju, A.T., Org. Lett., 2014, vol. 16, p. 5132. https://doi.org/10.1021/ol502490t

    Article  CAS  PubMed  Google Scholar 

  20. Pulina, N.A., Kuznetsov, A.S., Lisovenko, N.Yu., and Chemadurov, D.G., Russ. J. Org. Chem., 2014, vol. 50, p. 1783. https://doi.org/10.1134/S1070428014120124

    Article  CAS  Google Scholar 

  21. Boulos, L.S., Ewies, E.F., Ibrahim, N.M., and Mohram, M.E., Phosphorus, Sulfur Silicon Relat. Elem., 2014, vol. 189, p. 1706. https://doi.org/10.1080/10426507.2014.887077

    Article  CAS  Google Scholar 

  22. Korkusuz, E., Yildirim, I., and Iahin, E., Heterocycles, 2013, vol. 87, p. 2249. https://doi.org/10.3987/COM-13-12799

    Article  CAS  Google Scholar 

  23. Lisovenko, N.Yu. and Dryahlov, A.V., Chem. Heterocycl. Compd., 2014, vol. 50, p. 1. https://doi.org/10.1007/s10593-014-1439-x

    Article  CAS  Google Scholar 

  24. Kasimoullari, R., Maden, M., Yaglioglu, A.S., Mert, S., and Demirta, I., Indian J. Chem. Sect. B, 2015, vol. 54, p. 1134.

    Google Scholar 

  25. Maigali, S.S., El-Hussieny, M., and Soliman, F.M., J. Heterocycl. Chem., 2015, vol. 52, p. 15. https://doi.org/10.1002/jhet.1911

    Article  CAS  Google Scholar 

  26. Kasimoullari, R., Duran, H., Yaliolu, A., Mert, S., and Demirta, I., Monatsh. Chem., 2015, vol. 146, p. 1743. https://doi.org/10.1007/s00706-015-1450-7

    Article  CAS  Google Scholar 

  27. Korkusuz, E. and Yildirim, I., Helv. Chim. Acta, 2013, vol. 96, p. 1339. https://doi.org/10.1002/hlca.201200463

    Article  CAS  Google Scholar 

  28. Lisovenko, N.Yu., Merkushev, A.A., Nasibullina, E.R., Slepukhin, P.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2014, vol. 50, p. 759. https://doi.org/10.1134/S1070428014050261

    Article  CAS  Google Scholar 

  29. Koch, R., Blanch, R.J., and Wentrup, C., J. Org. Chem., 2014, vol. 79, p. 6978. https://doi.org/10.1021/jo5011087

    Article  CAS  PubMed  Google Scholar 

  30. Kayukova, L.A., Praliyev, K.D., Gut’yar, V.G., and Baitursynova, G.P., Russ. J. Org. Chem., 2015, vol. 51, p. 148. https://doi.org/10.1134/S1070428015020025

    Article  CAS  Google Scholar 

  31. Fofana, M., Dudognon, Y., Bertrand, L., Constantieux, T., Rodriguez, J., Ndiaye, I., Bonne, D., and Bugaut, X., Eur. J. Org. Chem., 2020, vol. 2020, p. 23. https://doi.org/10.1002/ejoc.202000460

    Article  CAS  Google Scholar 

  32. Horton, W.J., Hummel, C.E., and Jonson, H.W., J. Am. Chem. Soc., 1953, vol. 75, p. 944. https://doi.org/10.1021/ja01100a051

    Article  CAS  Google Scholar 

  33. Maslivets, A.N., Tarasova, O.P., and Andreichikov, Yu.S., Zh. Org. Khim., 1992, vol. 28, p. 1287.

    CAS  Google Scholar 

  34. Tarasova, O.P. and Maslivets, A.N., Konferebtsiya molodykh uchenykh PGU: Tezisy dokladov (Conference of Young Scientists of PGU: Abstracts of Reports), Perm’, 1991, p. 107.

  35. Maslivets, A.N. and Simonchik, O.L., Konferebtsiya molodykh uchenykh PGU: Tezisy dokladov (Conference of Young Scientists of PGU: Abstracts of Reports), Perm’, 1991, p. 12.

  36. Lisovenko, N.Yu., Russ. J. Org. Chem., 2018, vol. 54, p. 707. https://doi.org/10.1134/S1070428018050068

    Article  CAS  Google Scholar 

  37. Lisovenko, N.Yu., Kozlova, E.P., and Dmitriev, M.V., Vestn. PGNIU, Ser. Khim., 2017, vol. 7, p. 468. https://doi.org/10.17072/2223-1838-2017-4-468-475

    Article  Google Scholar 

  38. Obafemi, C.A., Adelani, P.O., Fadare, O.A., Akinpelu, D.A., and Famuyiwa, S, O., J. Mol. Struct., 2013, vol. 1049, p. 429. https://doi.org/10.1016/j.molstruc.2013.06.068

    Article  CAS  Google Scholar 

  39. Dai, Y., Hartke, R., Li, C., Yang, Q., Liu, J.O., and Wang, L.-X., ACS Chem. Biol., 2020, vol. 15, p. 2662. https://doi.org/10.1021/acschembio.0c00228

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Chen, X., Zhu, X., Ding, Y., and Shen, Y., J. Antibiot., 2011, vol. 64, p. 563. https://doi.org/10.1038/ja.2011.55

    Article  CAS  Google Scholar 

  41. Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P.R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., and Wood, P.A., J. Appl. Crystallogr., 2008, vol. 41, p. 466. https://doi.org/10.1107/S0021889807067908

    Article  CAS  Google Scholar 

  42. Igidov, N.M., Odegova, T.F., Tomilov, M.V., Syropyatov, B.Ya., and Vakhrin, M.I., RF Patent no. RU2303025C2, 2005.

  43. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2012.

  44. Becker, H.G.O., Beckert, R., Berger, V., Domshke, G., and Gewald, K., Organikum: Organisch-chemisches Grundpraktikum, Weinheim: Wiley, 2004, 22nd Edn.

  45. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release, 27-03-2014 CrysAlis171.NET).

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  48. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  49. Pershin, G.N., Metody eksperimental’noi khimioterapii (Methods of Experimental Chemotherapy), Moscow: Meditsina, 1971, p. 109.

  50. Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv (A Guide to Preclinical Trials of Medicines), Mironov, A.N., Eds., Moscow: Grif and K, 2012, pp. 509, 576.

  51. Eddy, N.B. and Leimbach, D.J., J. Pharmacol. Exp. Ther., 1953, vol. 107, p. 385.

    CAS  PubMed  Google Scholar 

  52. Rukovodstvo po soderzhaniyu i ispol’zovaniyu laboratornykh zhivotnykh (Guidelines for the Care and Use of Laboratory Animals), Belozertseva, I.V., Ed., Moscow: Irbis, 2017.

  53. Rukovodstvo R 1.2.3156-13 “Otsenka toksichnosti i opasnosti khimicheskikh veshchestv i ikh smesei dlya zdorov’ya cheloveka” (“Assessment of the Toxicity and Danger of Chemicals and Their Mixtures for Human Health”), Moscow: Federal’nyi tsentr gigieny i epidemiologii Rospotrebnadzora, 2014.

  54. Belen’kii, M.L., Elementy kolichestvennoi otsenki farmakologicheskogo effekta (Elements of Quantitative Evaluation of Pharmacological Effect), Leningrad: Meditsina, 1963.

Download references

Funding

The work was financially supported by the “Rational Subsoil Use” world-class Perm Scientific and Educational Center, 2023.

Author information

Authors and Affiliations

  1. Perm State University, 614990, Perm, Russia

    E. P. Kozlova, S. Y. Balandina, R. R. Makhmudov & N. Y. Lisovenko

  2. Federal Scientific Center for Medical and Preventive Technologies of Public Health Risk Management, 614045, Perm, Russia

    R. R. Makhmudov

Authors
  1. E. P. Kozlova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Y. Balandina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. R. Makhmudov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. Y. Lisovenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. Y. Lisovenko.

Ethics declarations

The authors of this work declare that they have 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

Kozlova, E.P., Balandina, S.Y., Makhmudov, R.R. et al. Synthesis and Antimicrobial and Analgesic Activity of Products of the Recyclization of 5-(Het)Aryl-4-(trifluoromethyl)furan-2,3-diones under the Action of Aromatic Amines. Russ J Org Chem 60, 221–230 (2024). https://doi.org/10.1134/S1070428024020064

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428024020064

Keywords:

Search

Navigation