Skip to main content
SpringerLink
Log in

Antiproliferative Activity Missing in 6-Substituted Polycarbonitrile Derivatives of 3-Azabicyclo[3.1.0]Hexane

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

The antiproliferative activity of 6-substituted polycarbonitrile derivatives of 3-azabicyclo[3.1.0]hexane was studied. It was established that the activity of the substances was directly related to the presence of a 6-substituent. Thus, 6-substituted derivatives of 3-azabicyclo[3.1.0]hexane did not possess antiproliferative activity and could be of interest only as potential antitussive and hypoglycemic drugs.

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 1.

Similar content being viewed by others

References

  1. W. Wang, Y. Mi, X.-P. Cao, and Z.-F. Shi, Org. Lett., 21(17), 6603 – 6607 (2019).

    Article  CAS  Google Scholar 

  2. D. L. Boger, C. W. Boyce, R. M. Garbaccio, and J. A. Goldberg, Chem. Rev., 97(3), 787 – 828 (1997).

    Article  CAS  Google Scholar 

  3. S. Gomi, D. Ikeda, H. Nakamura, H. Naganawa, et al., J. Antibiot. (Tokyo), 37(11), 1491 – 1494 (1984).

    Article  CAS  Google Scholar 

  4. B. Witkop, Y. Fujimoto, F. Irreverre, et al., J. Am. Chem. Soc., 93(14), 3471 – 3477 (1971).

    Article  CAS  Google Scholar 

  5. R. Ganorkar, A. Natarajan, A. Mamai, and J. S. Madalengoitia, J. Org. Chem., 71(13), 5004 – 5007 (2006).

    Article  CAS  Google Scholar 

  6. K. Shimamoto, M. Ishida, H. Shinozaki, and Y. Ohfune, J. Org. Chem., 56(13), 4167 – 4176 (1991).

    Article  CAS  Google Scholar 

  7. T. Morikawa, H. Sasaki, R. Hanai, et al., J. Org. Chem., 59(1), 97 – 103 (1994).

    Article  CAS  Google Scholar 

  8. S. R McCabe and P. Wipf, Synthesis, 51(1), 213 – 224 (2019).

    Article  CAS  Google Scholar 

  9. P. Chen, C. Zhu, R. Zhu, et al., Org. Biomol. Chem., 15, 1228 – 1235 (2017).

    Article  CAS  Google Scholar 

  10. G. Lunn, B. J. Banks, R. Crook, et al., Bioorg. Med. Chem. Lett., 21(15), 4608 – 4611 (2011).

    Article  CAS  Google Scholar 

  11. G. Lunn, L. R. Roberts, S. Content, et al., Bioorg. Med. Chem. Lett., 22(6), 2200 – 2203 (2012).

    Article  CAS  Google Scholar 

  12. D. Moffat, S. Patel, F. Day, et al., J. Med. Chem., 53(24), 8663 – 8678 (2010).

    Article  CAS  Google Scholar 

  13. J. A. Sattigeri, M. M. S. Andappan, K. Kishore, et al., Bioorg. Med. Chem. Lett., 18(14), 4087 – 4091 (2008).

    Article  CAS  Google Scholar 

  14. A. Mamai, R. Zhang, A. Natarajan, and J. S. Madalengoitia, J. Org. Chem., 66(2), 455 – 460 (2001).

    Article  CAS  Google Scholar 

  15. R. V. Golubev, A. Yu. Alekseeva, I. N. Bardasov, et al., Russ. J. Org. Chem., 47(3), 363 – 365 (2011).

    Article  CAS  Google Scholar 

  16. I. N. Bardasov, D. L. Mikhailov, A. Yu. Alekseeva, et al., Russ. J. Org. Chem., 51(6), 849 – 852 (2015).

    Article  CAS  Google Scholar 

  17. I. N. Bardasov, O. V. Kayukova, Ya. S. Kayukov, et al., Russ. J. Org. Chem., 45(9), 1325 – 1335 (2009).

    Article  CAS  Google Scholar 

  18. D. L. Boger and D. S. Johnson, Angew. Chem., Int. Ed. Engl., 35(13 – 14), 1438 – 1474 (1996).

    Article  CAS  Google Scholar 

  19. D. L. Boger, D. S. Johnson, and W. Wrasidlo, Bioorg. Med. Chem. Lett., 4(4), 631 – 636 (1994).

    Article  Google Scholar 

  20. F. F. Fleming, L. Yao, P. C. Ravikumar, L. Funk, and B. C. Shook, J. Med. Chem., 53, 7902 – 7917 (2010).

    Article  CAS  Google Scholar 

  21. A. Monks and D. Scudiero, J. Natl. Cancer Inst., 83(11), 757 – 766 (1991).

    Article  CAS  Google Scholar 

  22. https: // dtp.cancer.gov / discovery development/nci-60/cell_list.htm.

  23. GPM. 1.1.0014.15, State Pharmacopoeia of the Russian Federation, XIVth Ed., Vol. 1, (2018), pp. 319 – 369; http://femb.ru/femb/pharmacopea.php.

Download references

Acknowledgments

The work was performed in the framework of a State Task from the Ministry of Education and Science of Russia, Project No. 0849-2020-0003.

Author information

Authors and Affiliations

  1. I. N. Ul’yanov Chuvash State University, Cheboksary, Chuvash Republic, 428015, Russia

    I. N. Bardasov, A. Yu. Alekseeva, O. V. Ershov & M. A. Mar’yasov

Authors
  1. I. N. Bardasov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Yu. Alekseeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Ershov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. A. Mar’yasov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. N. Bardasov.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 54, No. 8, pp. 7 – 9, August, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bardasov, I.N., Alekseeva, A.Y., Ershov, O.V. et al. Antiproliferative Activity Missing in 6-Substituted Polycarbonitrile Derivatives of 3-Azabicyclo[3.1.0]Hexane. Pharm Chem J 54, 781–783 (2020). https://doi.org/10.1007/s11094-020-02273-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-020-02273-0

Keywords

Search

Navigation