Skip to main content
SpringerLink
Log in

Synthesis of N-Alkyl Enamino Ketones Based on 3-Acyl-4H-polyfluorochromen-4-ones and Their Antimicrobial Activity

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

Abstract

New N-substituted enamino ketones were synthesized by directed transformation of 3-acetyl- and 3-benzoyl-5,6,7,8-tetrafluoro-4H-chromen-4-ones by the action of highly basic primary amines as a result of opening of the pyranone ring and deacylation. The synthesizedN-hexyl and N-octyl derivatives were evaluated for fungistatic and bacteriostatic activities.

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

Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Lue, P. and Grenhill, J.V., Adv. Heterocycl. Chem., 1996, vol. 67, p. 207. https://doi.org/10.1016/S0065-2725(08)60072-0

    Article  CAS  Google Scholar 

  2. Gaber, H.M., Bagley, M.C., Muhammad, Z.A., and Gomha, S.M.,RSC Adv., 2017, vol. 7, p. 14562. https://doi.org/10.1039/C7RA00683G

    Article  CAS  Google Scholar 

  3. Stanovnic, B., Eur. J. Org. Chem., 2019, vol. 2019, nos. 31–32, p. 5120. https://doi.org/10.1002/ejoc.201900797

    Article  CAS  Google Scholar 

  4. Fu, L. and Wan, J.-P., Asian J. Org. Chem., 2019, vol. 8, p. 767. https://doi.org/10.1002/ajoc.201900196

    Article  CAS  Google Scholar 

  5. Eddington, N.D., Cox, D.S., Roberts, R.R., Stables, J.P., Powell, C.B., and Scott, K.R., Curr. Med. Chem., 2000, vol. 7, p. 417. https://doi.org/10.2174/0929867003375092

    Article  CAS  PubMed  Google Scholar 

  6. Negri, G., Kascheres, C., and Kascheres, A., J. Heterocycl. Chem., 2004, vol. 41, p. 461. https://doi.org/10.1002/jhet.5570410402

    Article  CAS  Google Scholar 

  7. Gaber, H.M. and Bagley, M.C., ChemMedChem, 2009, vol. 4, p. 1043. https://doi.org/10.1002/cmdc.200900006

    Article  CAS  PubMed  Google Scholar 

  8. Riyadh, S.M., Molecules, 2011, vol. 16, p. 1834. https://doi.org/10.3390/molecules16021834

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Kalita, U., Kaping, S., Nongkynrih, R., Sunn, M., Boiss, I., Singha, L.I., and Vishwakarma, J.N., Med. Chem. Res., 2014, vol. 24, p. 32. https://doi.org/10.1007/s00044-014-1086-x

    Article  CAS  Google Scholar 

  10. Theppawong, A., De Vreese, R., Vannecke, L., Grootaert, C., Van Camp, J., and D’hooghe, M., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 5650. https://doi.org/10.1016/j.bmcl.2016.10.068

    Article  CAS  PubMed  Google Scholar 

  11. De Vreese, R., Grootaert, C., D’Hoore, S., Theppawong, A., Van Damme, S., Van Bogaert, M., Van Camp, J., and D’hooghe, M., Eur. J. Med. Chem., 2016, vol. 123, p. 727. https://doi.org/10.1016/j.ejmech.2016.07.017

    Article  CAS  PubMed  Google Scholar 

  12. Dannhardt, G., Bauer, A., and Nowe, U., J. Prakt. Chem., 1998, vol. 340, p. 256. https://doi.org/10.1002/prac.19983400309

    Article  CAS  Google Scholar 

  13. Masocha, W., Kombian, S.B., and Edafiogho, I.O., Sci. Rep., 2016, vol. 6, p. 1. https://doi.org/10.1038/srep21582

    Article  CAS  Google Scholar 

  14. Ghoneim, O.M., Bill, A., Dhuguru, J., Szollosi, D.E., and Edafiogho, I.O., Bioorg. Med. Chem., 2018, vol. 26, p. 3890. https://doi.org/10.1016/j.bmc.2018.06.003

    Article  CAS  PubMed  Google Scholar 

  15. Kumar, R., Saha, N., Purohit, P., Garg, S.K., Seth, K., Meena, V.S., Dubey, S., Dave, K., Goyal, R., Sharma, S.S., Banerjee, U.C., and Chakraborti, A.K., Eur. J. Med. Chem., 2019, vol. 182, article ID 111601. https://doi.org/10.1016/j.ejmech.2019.111601

  16. Edafiogho, I.O., Hinko, C.N., Chang, H., Moore, J.A., Mulzac, D., Nicholson, J.M., Scott, K.R., J. Med. Chem., 1992, vol. 35, p. 2798. https://doi.org/10.1021/jm00093a012

    Article  CAS  PubMed  Google Scholar 

  17. Scott, K.R., Edafiogho, I.O., Richardson, E.L., Farrar, V.A., Moore, J.A., Tietz, E.I., Hinko, C.N., Chang, H., El-Assadi, A., and Nicholson, J.M., J. Med. Chem., 1993, vol. 36, p. 1947. https://doi.org/10.1021/jm00066a003

    Article  CAS  PubMed  Google Scholar 

  18. Scott, K.R., Rankin, G.O., Stables, J.P., Alexander, M.S., Edafiogho, I.O., Farrar, V.A., Kolen, K.R., Moore, J.A., Sims, L.D., and Tonnu, A.D., J. Med. Chem., 1995, vol. 38, p. 4033. https://doi.org/10.1021/jm00020a019

    Article  CAS  PubMed  Google Scholar 

  19. Okoro, C.O., Apraku, J., Okoromoba, E.O., and Fadeyi, O.O.,Lett. Drug Des. Discovery, 2013, vol. 10, p. 1024. https://doi.org/10.2174/15701808113109990064

    Article  CAS  Google Scholar 

  20. Amaye, I., Heinbockel, T., Woods, J., Wang, Z., Martin-Caraballo, M., and Jackson-Ayotunde, P., Int. J. Environ. Res. Public Health, 2018, vol. 15, p. 1784. https://doi.org/10.3390/ijerph15081784

    Article  CAS  PubMed Central  Google Scholar 

  21. Apraku, J. and Okoro, C.O., Bioorg. Med. Chem., 2019, vol. 27, p. 161. https://doi.org/10.1016/j.bmc.2018.11.033

    Article  CAS  PubMed  Google Scholar 

  22. Ghorab, M.M., Alsaid, M.S., Ghabour, H.A., and Fun, H.-K.,Asian J. Chem., 2014, vol. 26, p. 7424. https://doi.org/10.14233/ajchem.2014.17171

    Article  CAS  Google Scholar 

  23. Maryanoff, B.E., Ho, W., McComsey, D.F., Reitz, A.B., Grous, P.P., Nortey, S.O., Shank, R.P., Dubinsky, B., Taylor, R.J., Jr., and Gardocki, J.F.,J. Med. Chem., 1995, vol. 38, p. 16. https://doi.org/10.1021/jm00001a005

    Article  CAS  PubMed  Google Scholar 

  24. Maryanoff, B.E., Nortey, S.O., McNally, J.J., Sanfilippo, P.J., McComsey, D.F., Dubinsky, B., Shank, R.P., and Reitz, A.B., Bioorg. Med. Chem. Lett., 1999, vol. 9, p. 1547. https://doi.org/10.1016/S0960-894X(99)00240-1

    Article  CAS  PubMed  Google Scholar 

  25. Wu, W.-N., Mckown, L.A., and Reitz, A.B., Eur. J. Drug Metab. Pharmacokinet., 2006, vol. 31, p. 277. https://doi.org/10.1007/bf03190468

    Article  CAS  PubMed  Google Scholar 

  26. Dubois, L., Evanno, Y., Even, L., Gille, C., Malanda, A., Machnik, D., and Rakotoarisoa, N., Int. Patent Appl. no. WO 2007088277; Chem. Abstr., 2007, vol. 147, no. 257798.

  27. Ravi Kumar, A., Sathaiah, G., Chandra Shekhar, A., Raju, K., Shanthan Rao, P., Narsaiah, B., Raju, Y.K., and Murthy, U.S.N., J. Heterocycl. Chem., 2015, vol. 52, p. 235. https://doi.org/10.1002/jhet.2034

    Article  CAS  Google Scholar 

  28. Venepally, V., Prasad, R.B.N., Poornachandra, Y., Ganesh Kumar, C., and Jala, R.C.R., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 613. https://doi.org/10.1016/j.bmcl.2015.11.063

    Article  CAS  PubMed  Google Scholar 

  29. Cho, J.C., Crotty, M.P., White, B.P., and Worley, M.V., Pharmacotherapy, 2018, vol. 38, p. 108. https://doi.org/10.1002/phar.2050

    Article  CAS  PubMed  Google Scholar 

  30. Mohammed, H.H.H., Abuo-Rahma, G.E.A.A., Abbas, S.H., and Abdelhafez, E.M.N., Curr. Med. Chem., 2019, vol. 26, p. 3132. https://doi.org/10.2174/0929867325666180214122944

    Article  CAS  PubMed  Google Scholar 

  31. O’Hagan, D., J. Fluorine Chem., 2010, vol. 131, p. 1071. https://doi.org/10.1016/j.jfluchem.2010.03.003

    Article  CAS  Google Scholar 

  32. Haranahalli, K., Honda, T., and Ojima, I., J. Fluorine Chem., 2019, vol. 217, p. 29. https://doi.org/10.1016/j.jfluchem.2018.11.002

    Article  CAS  Google Scholar 

  33. Jerzmanowska, Z. and Podwiński, B., Monatsh. Chem., 1967, vol. 98, p. 1395. https://doi.org/10.1007/bf00909008

    Article  CAS  Google Scholar 

  34. Myannik, K.A., Yarovenko, V.N., Krayushkin, M.M., and Levchenko, K.S., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, p. 543. https://doi.org/10.1007/s11172-014-0466-1

    Article  CAS  Google Scholar 

  35. Shcherbakov, K.V., Bazhin, D.N., Burgart, Ya.V., and Saloutin, V.I., Chem. Heterocycl. Compd., 2015, vol. 51, p. 961. https://doi.org/10.1007/s10593-016-1805-y

    Article  CAS  Google Scholar 

  36. Shcherbakov, K.V., Artemyeva, M.A., Burgart, Ya.V., Evstigneeva, N.P., Gerasimova, N.A., Zilberberg, N.V., Kungurov, N.V., Saloutin, V.I., and Chupakhin, O.N., J. Fluorine Chem., 2019, vol. 226, article ID 109354. https://doi.org/10.1016/j.jfluchem.2019.109354

  37. Lawrence, S.A., Amines: Synthesis, Properties, and Applications, Cambridge: Cambridge Univ. Press, 2004.

  38. Cho, J., Hwang, I.S., Choi, H., Hwang, J.H., Hwang, J.S., and Lee, D.G., J. Microbiol. Biotechnol., 2012, vol. 22, p. 1457. https://doi.org/10.4014/jmb.1205.05041

    Article  CAS  PubMed  Google Scholar 

  39. Shirobokov, V.P., Meditsinskaya mikrobiologiya, virusologiya i immunologiya (Medical Microbiology, Virology, and Immunology), Vinnitsa: Nova Kniga, 2015, p. 157.

  40. Kubanova, A.A., Stepanova, Zh.V., Gus’kova, T.A., Pushkina, T.V., Krylova, L.Yu., Shilova, I.B., and Trenin, A.S., Rukovodstvo po provedeniyu doklinicheskikh issledovanii lekarstvennykh sredstv (A Guide to Preclinical Trials of Medicines), Mironov, A.N., Ed., Moscow: Grif i K, 2012, part 1, p. 578.

  41. Performance Standards for Antimicrobial Susceptibility Testing, Clinical and Laboratory Standards Institute (CLSI), 24th ed., CLSI document M100-S24, 2014, vol. 34, p. 84.

Download references

ACKNOWLEDGMENTS

This study was performed using the facilities of the Spectroscopy and Analysis of Organic Compounds joint center (Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences). The microbiological study was performed at the Ural Research Institute of Dermatovenerology and Immunopathology.

Funding

This study was performed under financial support by the Russian Foundation for Basic Research and by the Ministry of Industries and Science of Sverdlovsk oblast (project no. 20-43-660011).

Author information

Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620990, Yekaterinburg, Russia

    K. V. Shcherbakov, M. A. Artemyeva, Ya. V. Burgart & V. I. Saloutin

  2. Yeltsin Ural Federal University, 620002, Yekaterinburg, Russia

    Ya. V. Burgart & V. I. Saloutin

  3. Ural Research Institute of Dermatovenerology and Immunopathology, 620076, Yekaterinburg, Russia

    N. A. Gerasimova & N. P. Evstigneeva

Authors
  1. K. V. Shcherbakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. Artemyeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ya. V. Burgart
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. A. Gerasimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. P. Evstigneeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. I. Saloutin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. V. Shcherbakov.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shcherbakov, K.V., Artemyeva, M.A., Burgart, Y.V. et al. Synthesis of N-Alkyl Enamino Ketones Based on 3-Acyl-4H-polyfluorochromen-4-ones and Their Antimicrobial Activity. Russ J Org Chem 56, 1606–1612 (2020). https://doi.org/10.1134/S1070428020090171

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020090171

Keywords:

Search

Navigation