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Russian Journal of General Chemistry

, Volume 88, Issue 6, pp 1266–1269 | Cite as

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

  • V. B. Sokolov
  • A. Yu. Aksinenko
  • T. V. Goreva
  • T. A. Epishina
  • A. N. Samsonova
Letters to the Editor
  • 13 Downloads

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.

Keywords

carbazoles tetrahydrocarbazoles tetrahydro-γ-carbolines terminal diazidoalkanes 1,4-substituted 1,2,3-triazoles 1,3-dipolar cycloaddition 

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References

  1. 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.2013.10.016CrossRefGoogle Scholar
  2. 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.0909133107CrossRefGoogle Scholar
  3. 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.21434CrossRefGoogle Scholar
  4. 4.
    Elisabeth, B.J. and Woodhead, M.M.M., WO Patent 2007096576A1, 2007; C. A., 2007, vol. 147, p. 322966.Google Scholar
  5. 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.2011.03.039CrossRefGoogle Scholar
  6. 6.
    Mahulikar, P.P., Dalal, D.S., and Pawar, N.S., Org. Chem., 2006, vol. 2, nos. 5–6, p.174.Google Scholar
  7. 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.2010.01.159CrossRefGoogle Scholar
  8. 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. 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 10.2174/092986709788612701CrossRefGoogle Scholar
  10. 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.2014.09.004CrossRefGoogle Scholar
  11. 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/jm981093mCrossRefGoogle Scholar
  12. 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.2012.07.080CrossRefGoogle Scholar
  13. 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-2012-121732CrossRefGoogle Scholar
  14. 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.10.13CrossRefGoogle Scholar
  15. 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.CrossRefGoogle Scholar
  16. 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/s11172-015-0925-3CrossRefGoogle Scholar
  17. 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/s11172-015-1017-0CrossRefGoogle Scholar
  18. 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/srep13164Google Scholar
  19. 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/S1070363215060158CrossRefGoogle Scholar
  20. 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.201201201CrossRefGoogle Scholar
  21. 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/c4ob00686kCrossRefGoogle Scholar
  22. 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/jm00107a048CrossRefGoogle Scholar
  23. 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/jm201504sCrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • V. B. Sokolov
    • 1
  • A. Yu. Aksinenko
    • 1
  • T. V. Goreva
    • 1
  • T. A. Epishina
    • 1
  • A. N. Samsonova
    • 1
  1. 1.Institute of Physiologically Active CompoundsRussian Academy of SciencesChernogolovkaRussia

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