Skip to main content
SpringerLink
Log in

Synthesis of (S)-N-Ethyl-2-(5-methylidene-4-oxocyclopent-2-en-1-yl)acetamide―A Model exo-Methylidenecyclopentenone Bioisoster of Prostamides

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

Abstract

exo-Methylidenecyclopentenonee amide is synthesized from methyl 2-[({(1R,2R,5R)-2-{[(tert-butyl(dimethyl)silyl]oxymethyl})-5-(trimethylsilyl)cyclopent-3-en-1-yl]acetate.

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

REFERENCES

  1. Gimazetdinov, A.M., Khalfitdinova, L.A., and Mifakhov, M.S., Mendeleev Commun., 2013, vol. 23, p. 321. https://doi.org/10.1016/j.tet.2013.09.047

    Article  CAS  Google Scholar 

  2. Vostricov, N.S., Spirikhin, L.V., Lobov, A.N., Gimazetdinov, A.M., Zileeva, Z.R., Vakhitova, Y.V., Macaev, Z.R., Pivnitsky, K.K., and Miftakhov, M.S., Mendeleev Commun. 2019, vol. 29, p. 372. https://doi.org/10.1016/j.mencom.2019.07.003

  3. Loza, V.V., Gimazetdinov, A.M., and Miftakhov, M.S., Russ. J. Org. Chem., 2018, vol. 54, p. 1585. https://doi.org/10.1134/S1070428018110015

    Article  CAS  Google Scholar 

  4. Bie, Q., Dong, H., Jin, C., Zhang, H., and Zhang, B., Am. J. Transl. Res., 2018, vol. 10, p. 648.

    CAS  PubMed  PubMed Central  Google Scholar 

  5. Ladin, D.A., Soliman, E., Escobedo, R., Fitzgerald, T.L., Yang, L.V., Burns, C., and Dross, R.V., Mol. Cancer Ther., 2017, vol. 16, p. 838. https://doi.org/10.1158/1535-7163.MCT-16-0484

    Article  CAS  PubMed  Google Scholar 

  6. Ladin, D.A., Nelson, M.M., Cota, E., Colonna, C., Burns, C., Robidoux, J., Fisher-Wellman, K.H., and Van Dross-Anderson, R., Oncotarget., 2022, vol. 13, p. 1380. https://doi.org/10.18632/oncotarget.28334

    Article  PubMed  PubMed Central  Google Scholar 

  7. Gimazetdinov, A.M., Gataullin, S.S., Bushmarinov, I.S., and Miftakhov, M.S., Tetrahedron, 2012, vol. 68, p. 5754. https://doi.org/10.1016/j.tet.2012.05.036

    Article  CAS  Google Scholar 

  8. Gimazetdinov, A.M., Al’mukhametov, A.Z., and Miftakhov, M.S., Russ. J. Org. Chem., 2019, vol. 55, p. 831. https://doi.org/10.1134/S1070428019060137

    Article  CAS  Google Scholar 

  9. Aralbaeva, G.V., Al’mukhametov, A.Z., and Gimazetdinov, A.M., Russ. J. Org. Chem., 2022, vol. 58, p. 1589. https://doi.org/10.1134/S1070428022110057

    Article  Google Scholar 

  10. Gimazetdinov, A.M., Al’mukhametov, A.Z., Loza, V.V., Spirikhin, L.V., and Miftakhov, M.S., Mendeleev Commun., 2018, vol. 28, p. 546. https://doi.org/10.1016/j.mencom.2018.09.033

    Article  CAS  Google Scholar 

  11. Gimazetdinov, A.M., Al’mukhametov, A.Z., and Miftakhov, M.S., New J. Chem., 2022, vol. 46, p. 6708. https://doi.org/10.1039/d2nj01003h

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

Spectral measurements and theoretical calculations were performed using the equipment of the Khimiya Center for Collective Use, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

The work was funded through the state assignment of the Ministry of Science and Higher Education of the Russian Federation (project no. AAAA-A17-117011910032-4).

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    A. M. Gimazetdinov, Z. R. Makaev & M. S. Miftakhov

Authors
  1. A. M. Gimazetdinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Z. R. Makaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. S. Miftakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. M. Gimazetdinov.

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

Gimazetdinov, A.M., Makaev, Z.R. & Miftakhov, M.S. Synthesis of (S)-N-Ethyl-2-(5-methylidene-4-oxocyclopent-2-en-1-yl)acetamide―A Model exo-Methylidenecyclopentenone Bioisoster of Prostamides. Russ J Org Chem 60, 231–236 (2024). https://doi.org/10.1134/S1070428024020076

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428024020076

Keywords:

Search

Navigation