Skip to main content
SpringerLink
Log in

New approach to 5-arylamino-4-(5-aryloxyfuran-2-yl)pyrimidines: synthesis and antibacterial activity

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A method for the synthesis of previously unknown 5-arylamino-substituted 4-(5-aryloxy-furan-2-yl)pyrimidines containing methyl and methoxy groups at different positions of the aryl substituents was developed. The method is based on the combination of the Buchwald-Hartwig cross-coupling reaction with various anilines and nucleophilic substitution of the nitro group by phenolate anions. All the new compounds were screened against 15 different pathogenic bacterial strains. 4-[5-(3,4,5-Trimethoxyphenoxy)furan-2-yl]-substituted pyrimidines were found to possess high antibacterial activity against gonococcal infections, in some cases ten times higher than that of the commercial drug Spectinomycin.

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

Similar content being viewed by others

References

  1. G. Cheng, S. P. Muench, Y. Zhou, G. A. Afanador, E. J. Mui, A. Fomovska, B. S. Lai, S. T. Prigge, S. Woods, C. W. Roberts, M. R. Hickman, P. J. Lee, S. E. Leed, J. M. Auschwitz, D. W. Rice, R. McLeod, Bioorg. Med. Chem. Lett., 2013, 23, 2035.

    Article  CAS  Google Scholar 

  2. C.-L. Chang, Chem. Pharm. Bull., 2009, 57, 550.

    Article  CAS  Google Scholar 

  3. M. Ryota, O. Kohei, T. Takamasa, S. Yasumasa, Pat. WO 2019189731 A1, 2019.

  4. E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Eur. J. Med. Chem., 2015, 97, 225.

    Article  CAS  Google Scholar 

  5. E. V. Verbitskiy, S. A. Baskakova, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Bioorg. Med. Chem., 2016, 24, 3771.

    Article  CAS  Google Scholar 

  6. E. V. Verbitskiy, S. A. Baskakova, N. A. Gerasimova, N. P. Evstigneeva, N. V. Zil’berberg, N. V. Kungurov, M. A. Kravchenko, S. N. Skornyakov, M. G. Pervova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Bioorg. Med. Chem. Lett., 2017, 27, 3003.

    Article  CAS  Google Scholar 

  7. E. V. Verbitskiy, S. A. Baskakova, N. A. Gerasimova, N. P. Evstigneeva, N. V. Zil’berberg, N. V. Kungurov, M. A. Kravchenko, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Mendeleev Commun., 2018, 28, 393.

    Article  CAS  Google Scholar 

  8. F. Lieb, K. Eiter, Lieb. Ann. Chem., 1972, 761, 130.

    Article  CAS  Google Scholar 

  9. M. Ogawa, K. Sakuma, H. Okamoto, J. Koyanagi, K. Nakayama, A. Tanaka, K. Yamamoto, J. Heterocyclic Chem., 2007, 44, 1145.

    Article  CAS  Google Scholar 

  10. S. Gavade, K. Padiya, S. Bajare, R. Balaskar, D. Mane, J. Heterocyclic Chem., 2011, 48, 458.

    Article  CAS  Google Scholar 

  11. X. Tang, L. Tong, M. Yao, Q. Liang, X. Wang, H. Yu, Synlett., 2017, 28, 1187.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620108, Ekaterinburg, Russian Federation

    E. V. Verbitskiy, S. A. Baskakova, G. L. Rusinov & V. N. Charushin

  2. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    E. V. Verbitskiy, G. L. Rusinov & V. N. Charushin

Authors
  1. E. V. Verbitskiy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Baskakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. N. Charushin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Verbitskiy.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 937–942, May, 2021.

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (Agreement No. 075-15-2020-777).

This work does not involve human participants and animal subjects.

The authors declare no competing interest requiring disclosure in the present article.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Verbitskiy, E.V., Baskakova, S.A., Rusinov, G.L. et al. New approach to 5-arylamino-4-(5-aryloxyfuran-2-yl)pyrimidines: synthesis and antibacterial activity. Russ Chem Bull 70, 937–942 (2021). https://doi.org/10.1007/s11172-021-3170-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3170-y

Key words

Search

Navigation