Skip to main content
SpringerLink
Log in

Copper-catalyzed 1,3-Dipolar Cycloaddition of Substituted N-Propargylindoles and Terminal Diazidoalkanes

  • Letters to the Editor
  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition was studied of substituted N-propargylindoles and diazidoalkanes leading to symmetric conjugates of substituted indoles with bistriazole-containing spacer.

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

References

  1. Nagesh, H.N., Naidu, K.M., Rao, D.H., Sridevi, J.P., Sriram, D., Yogeeswari, P., and Sekhar, K.V.G.C., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 24, p. 6805. doi 10.1016/j.bmcl.2013.10.016

    Article  CAS  PubMed  Google Scholar 

  2. Zhou, B., He, Y., Zhang, X., Xu, J., Luo, Y., Wang, Y., Franzblau, S.G., Yang, Z., Chan, R.J., Liu, Y., Zheng, J., and Zhang, Z.Y., Proc. Natl. Acad. Sci. USA, 2010, vol. 107, p. 4573. doi 10.1073/pnas.0909133107

    Article  PubMed  Google Scholar 

  3. Bachurin, S.O., Bovina, E.V., and Ustyugov, A.A., Med. Res. Rev., 2017, vol. 37, no. 5, p. 1186. doi 10.1002/med.21434

    Article  CAS  Google Scholar 

  4. Elisabeth, B.J. and Woodhead, M.M.M., WO Patent 2007096576A1, 2007; C. A., 2007, vol. 147, p. 322966.

  5. Thomas, K.D., Adhikari, A.V., Chowdhury, I.H., Sumesh, E., and Pal, N.K., Eur. J. Med. Chem., 2011, vol. 46, no. 6, p. 2503. doi 10.1016/j.ejmech.2011.03.039

    Article  CAS  PubMed  Google Scholar 

  6. Mahulikar, P.P., Dalal, D.S., and Pawar, N.S., Org. Chem., 2006, vol. 2, nos. 5–6, p.174.

    CAS  Google Scholar 

  7. Zhang, F.-F., Gan, L.-L., and Zhou, C.-H., Bioorg. Med. Chem. Lett., 2010, vol. 20, no. 6, p. 1881. doi 10.1016/j.bmcl.2010.01.159

    Article  CAS  PubMed  Google Scholar 

  8. Yaqub, G., Hannan, A., Akbar, E., Usman, M., Hamid, A., Sadiq, Z., and Iqbal, M., J. Chem., 2013, ID 818739. doi 10.1155/2013/818739.

    Google Scholar 

  9. Thevissen, K., Marchand, A., Chaltin, P., Meert, E.M.K., and Cammue, B.P.A., Curr. Med. Chem., 2009, vol. 16, no. 17, p. 2205. doi 10.2174/092986709788612701

    Article  CAS  PubMed  Google Scholar 

  10. Giraud, F., Bourhis, M., Nauton, L., Théry, V., Herfindal, L., Døskeland, S.O., Anizon, F., and Moreau, P., Bioorg. Chem., 2014, vol. 57, p. 108. doi 10.1016/j.bioorg.2014.09.004

    Article  CAS  PubMed  Google Scholar 

  11. Guillonneau, C., Pierre, A., Charton, Y., Guilbard, N., Berthier, L.K., Leonce, S., Michael, A., Bisagni, E., and Atassi, G., J. Med. Chem., 1999, vol. 42, no. 12, p. 2191. doi 10.1021/jm981093m

    Article  CAS  PubMed  Google Scholar 

  12. Bandgar, B.P., Adsul, L.K., Chavan, H.V., Jalde, S.S., Shringare, S.N., Shaikh, R., Meshram, R.J., Gacche, R.N., and Masand, V., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 18, p. 5839. doi 10.1016/j.bmcl.2012.07.080

    Article  CAS  PubMed  Google Scholar 

  13. Peters, O.M., Connor-Robson, N., Sokolov, V.B., Aksinenko, A.Yu., Kukharsky, M.S., Bachurin, S.O., Ninkina, N.N., and Buchman, V.L., J. Alzheimer’s Dis., 2013, vol. 33, no. 4, p. 1041. doi 10.3233/JAD-2012-121732

    Article  CAS  Google Scholar 

  14. Sokolova, N.V., Nenajdenko, V.G., Sokolov, V.B., Vinogradova, D.V., Shevtsova, E.F., Dubova, L.G., and Bachurin, S.O., Beilstein J. Org. Chem., 2014, vol. 10, p. 155. doi 10.3762/bjoc.10.13

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Sokolov, V.B., Aksinenko, A.Yu., and Bachurin, S.O., Russ. J. Gen. Chem., 2014, vol. 84, no. 9, p. 1694. doi 10.1134/S1070363214090084.

    Article  CAS  Google Scholar 

  16. Sokolov, V.B., Aksinenko, A.Yu., Epishina, T.A., Goreva, T.V., Grigor’ev, V.V., Gabrel’yan, A.V., and Bachurin, S.O., Russ. Chem. Bull., 2015, vol. 64, no. 3, p. 718. doi 10.1007/s11172-015-0925-3

    Article  CAS  Google Scholar 

  17. Bachurin, S.O., Sokolov, V.B., Aksinenko, A.Yu., Epishina, T.A., Goreva, T.V., Gabrel’yan, A.V., and Grigor’ev, V.V., Russ. Chem. Bull., 2015, vol. 64, no. 6, p. 1452. doi 10.1007/s11172-015-1017-0

    Article  CAS  Google Scholar 

  18. Makhaeva, G.F., Lushchekina, S.V., Boltneva, N.P., Sokolov, V.B., Grigoriev, V.V., Serebryakova, O.G., Vikhareva, E.A., Aksinenko, A.Yu., Barreto, G.E., Bachurin, S.O., and Aliev, G., Sci. Rep., 2015, p. 13164. doi 10.1038/srep13164

    Google Scholar 

  19. Sokolov, V.B., Aksinenko, A.Yu., Epishina, T.A., Goreva, T.V., Gabrel’yan, A.V., Dranii, O.A., Grigor’-ev, V.V., and Bachurin, S.O., Russ. J. Gen. Chem., 2015, vol. 85, no. 6, p. 1452. doi 10.1134/S1070363215060158

    Article  CAS  Google Scholar 

  20. Betzler, F.M., Klapoetke, T.M., and Sproll, S.M., Eur. J. Org. Chem., 2013, vol. 2013, no. 3, p. 509. doi 10.1002/ejoc.201201201

    Article  CAS  Google Scholar 

  21. Kolli, S.K., Prasad, B., Babu, P.V., Ashfaq, M.A., Ehtesham, N.Z., Raju, R.R., and Pal, M., Org. Biomol. Chem., 2014, vol. 12, no. 12, p. 6080. doi 10.1039/c4ob00686k

    Article  CAS  PubMed  Google Scholar 

  22. Walser, A., Flynn, T., Mason, C., Crowley, H., Maresca, K., Yaremko, B., and O'Donnel, M., J. Med. Chem., 1991, vol. 34, no. 3, p. 1209. doi 10.1021/jm00107a048

    Article  CAS  PubMed  Google Scholar 

  23. Schiefer, I.T., Vande Vrede, L., Fa’, M., Arancio, O., and Thatcher, G.R.J., J. Med. Chem., 2012, vol. 55, no. 7, p. 3076. doi 10.1021/jm201504s

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physiologically Active Compounds, Russian Academy of Sciences, Severnyi proezd 1, Chernogolovka, 142432, Russia

    V. B. Sokolov, A. Yu. Aksinenko, T. V. Goreva, T. A. Epishina & A. N. Samsonova

Authors
  1. V. B. Sokolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Yu. Aksinenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. V. Goreva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. A. Epishina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. N. Samsonova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. B. Sokolov.

Additional information

Original Russian Text © V.B. Sokolov, A.Yu. Aksinenko, T.V. Goreva, T.A. Epishina, A.N. Samsonova, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 6, pp. 1044–1047.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sokolov, V.B., Aksinenko, A.Y., Goreva, T.V. et al. Copper-catalyzed 1,3-Dipolar Cycloaddition of Substituted N-Propargylindoles and Terminal Diazidoalkanes. Russ J Gen Chem 88, 1266–1269 (2018). https://doi.org/10.1134/S1070363218060361

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218060361

Keywords

Search

Navigation