Skip to main content
SpringerLink
Log in

Synthesis and antiviral properties of new derivatives of 2-(alkylsulfanyl)-6-[1-(2,6-difluorophenyl)cyclopropyl]-5-methylpyrimidin-4(3H)-one

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

Abstract

Based on 2-(2,6-difluorophenyl)acetonitrile a synthesis was performed of new bioisosteric prochiral analogs of anti-HIV-1 active derivatives of 2-alkoxy-6-benzylpyrimidin-4(3Н)-one that we had previously obtained. The study using infected and nonifected strains of cells MT-4 made it possible to find in all prepared compounds a high anti-HIV activity whereas the cytotoxicity of the substances depended strongly on the structure of the alkylsulfanyl fragment of the molecule.

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. Artico, M., Drugs of the Future, 2002, vol. 27, p. 159.

    Article  CAS  Google Scholar 

  2. Yang, S., Chen, F.E., and De Clercq, E., Cur. Med. Chem., 2012, vol. 19, p. 152.

    Article  CAS  Google Scholar 

  3. Novakov, I.A., Artico, M., Mai, A., Rotili, D., Orlinson, B.S., Brunilina, L.L., and Nawrozkij, M.B., Russ. Chem. Bull., 2012, vol. 61, p. 1399.

    Article  CAS  Google Scholar 

  4. Rotili, D., Tarantino, D., Nawrozkij, M.B., Babushkin, A.S., Botta, G., Marrocco, B., Cirilli, R., Menta, S., Badia, R., Crespan, E., Ballante, F., Ragno, R., Esté, J.A., Maga, G., and Mai, A., J. Med. Chem., 2014, vol. 57, p. 5212.

    Article  CAS  Google Scholar 

  5. Babushkin, A.S., Nawrozkij, M.B., Novakov, I.A., and Yablokov, A.S., Macroheterocycles, 2016, vol. 9, p. 50.

    Article  Google Scholar 

  6. Schuetz, F., Sauter, H., Goetz, N., Wild, J., Wolf, H.-J., Doetzer, R., Lorenz, G., Ammermann, E., Kuenast, C., and Kardorff, U., US Patent no. 5371268, 1994.

  7. Pauwels, R., Balzarini, J., Baba, M., Snoeck, R., Schols, D., Herdewijn, P., Desmyter, J., and De Clercq, E., J. Virol. Methods, 1988, vol. 20, p. 309.

    Article  CAS  Google Scholar 

  8. Mai, R., Artico, M., Rotili, D., Tarantino, D., Clotet-Codina, I., Armand-Ugón, M., Ragno, R., Simeoni, S., Sbardella, G., Nawrozkij, M.B., Samuele, A., Maga, G., and Esté, J.A., J. Med. Chem., 2007, vol. 50, p. 5412.

    Article  CAS  Google Scholar 

  9. Rotili, D., Samuele, A., Tarantino, D., Ragno, R., Musmuca, I., Ballante, F., Botta, G., Morera, L., Pierini, M., Cirilli, R., Nawrozkij, M.B., Gonzalez, E., Clotet, B., Artico, M., Esté, J.A., Maga, G., and Mai, A., J. Med. Chem., 2012, vol. 55, p. 3558.

    Article  CAS  Google Scholar 

  10. Tietze, L.-F. and Eicher, T., Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, Stuttgart Georg Thieme, 1991.

    Book  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Volgograd State Technical University, pr. Lenina 28, Volgograd, 400005, Russia

    I. A. Novakov, A. S. Yablokov, B. S. Orlinson, M. B. Navrotskii, I. A. Kirillov, A. A. Vernigora & A. S. Babushkin

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

    V. V. Kachala

  3. Rega Institute for Medical Research, Leuven, Belgium

    D. Schols

Authors
  1. I. A. Novakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Yablokov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. S. Orlinson
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. B. Navrotskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. A. Kirillov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. A. Vernigora
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. S. Babushkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. V. V. Kachala
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. D. Schols
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. S. Babushkin.

Additional information

Original Russian Text © I.A. Novakov, A.S. Yablokov, B.S. Orlinson, M.B. Navrotskii, I.A. Kirillov, A.A. Vernigora, A.S. Babushkin, V.V. Kachala, D. Schols, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 8, pp. 1195–1200.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Novakov, I.A., Yablokov, A.S., Orlinson, B.S. et al. Synthesis and antiviral properties of new derivatives of 2-(alkylsulfanyl)-6-[1-(2,6-difluorophenyl)cyclopropyl]-5-methylpyrimidin-4(3H)-one. Russ J Org Chem 52, 1188–1193 (2016). https://doi.org/10.1134/S1070428016080169

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428016080169

Search

Navigation