Advertisement

Russian Journal of Organic Chemistry

, Volume 50, Issue 6, pp 846–853 | Cite as

Synthesis and properties of 2-azahetarylaminomethylidene 1,3-dicarbonyl compounds

  • Yu. S. Kudyakova
  • Ya. V. Burgart
  • V. I. Saloutin
Article
  • 62 Downloads

Abstract

Reactions of 2-ethoxymethylidene 1,3-dicarbonyl compounds with pyridine-2,6- and pyrimidine-4,5-diamines gave the corresponding 2-hetarylaminomethylidene derivatives. Depending on the initial reactant structure, the formation of mono-and/or bis-condensation products is possible. Hetarylaminomethylidene derivatives showed a moderate tuberculostatic effect. 2-Pyridinylaminomethylidene 3-oxo esters were used as ligands to obtain coordination compounds with d- and f-metal ions.

Keywords

Minimum Inhibitory Concentration Diamine Dene Ethyl Acetoacetate Isonicotinic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Sato, M., Kawakami, H., Motomura, T., Aramaki, H., Matsuda, T., Yamashita, M., Ito, Y., Matsuzaki, Y., Yamataka, K., Ikeda, S., and Shinkai, H., J. Med. Chem., 2009, vol. 52, p. 4869.CrossRefGoogle Scholar
  2. 2.
    Rimland, J., Dunne, A., Hunjan, S.S., Sasse, R., Uings, I., Montanari, D., Caivano, M., Shah, P., Standing, D., Gray, D., Brown, D., Cairns, W., Trump, R., Smith, P.W., Bertheleme, N., Alessandro, P.D., Gul, S., Vimal, M., Smith, D.N., and Watson, S.P., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 2340.CrossRefGoogle Scholar
  3. 3.
    Pryadeina, M.V., Burgart, Ya.V., Saloutin, V.I., Sadchikova, E.V., and Ulomskii, E.N., Heterocycles, 2009, vol. 78, p. 435.CrossRefGoogle Scholar
  4. 4.
    Obermayer, D., Glasnov, T.N., and Kappe, C.O., J. Org. Chem., 2011, vol. 76, p. 6657.CrossRefGoogle Scholar
  5. 5.
    Pryadeina, M.V., Denisova, A.B., Burgart, Ya.V., and Saloutin, V.I., Russ. J. Org. Chem., 2008, vol. 44, p. 1811.CrossRefGoogle Scholar
  6. 6.
    Weber, B., Kaps, E., Obel, J., and Bauer, W., Z. Anorg. Allg. Chem., 2008, vol. 634, p. 1421.CrossRefGoogle Scholar
  7. 7.
    Schlamp, S., Weber, B., Naikb, A.D., and Garcia, Y., Chem. Commun., 2011, vol. 47, p. 7152.CrossRefGoogle Scholar
  8. 8.
    Lager, E., Andersson, P., Nilsson, J., Pettersson, I., Nielsen, E.O., Nielsen, M., Sterner, O., and Liljefors, T., J. Med. Chem., 2006, vol. 49, p. 2526.CrossRefGoogle Scholar
  9. 9.
    Reis, R. da R., Azevedo, E.C., de Souza, M.C.B.V., Ferreira, V.F., Montenegro, R.C., Arau’jo, A.J., Pessoa, C., Costa-Lotufo, L.V., de Moraes, M.O., Filho, J.D.B.M., de Souza, A.M.T., de Carvalho, N.C., Castro, H.C., Rodrigues, C.R., and Vasconcelos, T.R.A., Eur. J. Med. Chem., 2011, vol. 46, p. 1448.CrossRefGoogle Scholar
  10. 10.
    Xu, J., Cole, D.C., Chang, C.-P.B., Ayyad, R., Asselin, M., Hao, W., Gibbons, J., Jelinsky, S.A., Saraf, K.A., and Park, K., J. Med. Chem., 2008, vol. 51, p. 4115.CrossRefGoogle Scholar
  11. 11.
    Kudyakova, Yu.S., Bazhin, D.N., Goryaeva, M.V., Burgart, Ya.V., and Saloutin, V.I., Russ. Chem. Rev., 2014, vol. 83, no. 2, p. 120.CrossRefGoogle Scholar
  12. 12.
    Bazhin, D.N., Kudyakova, Yu.S., Gorbunova, T.I., Kozhevnikova, N.S., Suntsov, A.Yu., Burgart, Ya.V., Rempel’, A.A., Saloutin, V.I., and Chupakhin, O.N., Russ. J. Org. Chem., 2013, vol. 49, p. 315.CrossRefGoogle Scholar
  13. 13.
    Mikhaleva, M.A., Chem. Heterocycl. Compd., 2003, vol. 39, no. 8, p. 1032.CrossRefGoogle Scholar
  14. 14.
    Bazhin, D.N., Kudyakova, Yu.S., Gorbunova, T.I., Burgart, Ya.V., Zapevalov, A.Ya., and Saloutin, V.I., Russ. J. Gen. Chem., 2013, vol. 83, p. 1330.CrossRefGoogle Scholar
  15. 15.
    Kudyakova, Yu.S., Bazhin, D.N., Burgart, Ya.V., Saloutin, V.I., and Chupakhin, O.N., Russ. J. Org. Chem., 2013, vol. 49, p. 469.CrossRefGoogle Scholar
  16. 16.
    Kudyakova, Yu.S., Goryaeva, M.V., Burgart, Ya.V., Saloutin, V.I., and Slepukhin, P.A., Russ. Chem. Bull., Int. Ed., 2009, vol. 58, no. 6, p. 1241.CrossRefGoogle Scholar
  17. 17.
    Kudyakova, Yu.S., Goryaeva, M.V., Burgart, Ya.V., and Saloutin, V.I., Russ. J. Org. Chem., 2010, vol. 46, p. 1780.CrossRefGoogle Scholar
  18. 18.
    Kudyakova, Yu.S., Goryaeva, M.V., Burgart, Ya.V., Slepukhin, P.A., and Saloutin, V.I., Russ. Chem. Bull., Int. Ed., 2010, vol. 59, no. 8, p. 1582.CrossRefGoogle Scholar
  19. 19.
    Kudyakova, Yu.S., Goryaeva, M.V., Burgart, Ya.V., and Saloutin, V.I., Russ. J. Org. Chem., 2011, vol. 47, p. 331.CrossRefGoogle Scholar
  20. 20.
    Parameswaran, K., Sivaguru, P., and Lalitha, A., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 3873.CrossRefGoogle Scholar
  21. 21.
    Hodous, B.L., Liu-Bujalski, L., Jones, R., Bankston, D., Johnson, T.L., Mochalkin, I., Nguyen, N., Qiu, H., Goutopoulos, A., and Brugger, N., WO Patent Appl. no. 12 170 976; Chem. Abstr., 2012, vol. 158, no. 77 295.Google Scholar
  22. 22.
    Baraldi, P.G., Baraldi, S., Saponaro, G., Preti, D., Romagnoli, R., Piccagli, L., Cavalli, A., Recanatini, M., Moorman, A.R., Abdel Zaid, N., Varani, K., Borea, P.A., and Tabrizi, M.A., J. Med. Chem., 2012, vol. 55, p. 797.CrossRefGoogle Scholar
  23. 23.
    McGowan, D., Nyanguile, O., Cummings, M.D., Vendeville, S., Vandyck, K., Van den Broeck, W., Boutton, C.W., De Bondt, H., Quirynen, L., Amssoms, K., Bonfanti, J.-F., Last, S., Rombauts, K., Tahri, A., Hu, L., Delouvroy, F., Vermeiren, K., Vandercruyssen, G., Van der Helm, L., Cleiren, E., Mostmans, W., Lory, P., Pille, G., Van Emelen, K., Fanning, G., Pauwels, F., Lin, T.-I., Simmen, K., and Raboisson, P., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 2492.CrossRefGoogle Scholar
  24. 24.
    Mai, A., Perrone, A., Nebbioso, A., Rotili, D., Valente, S., Tardugno, M., Massa, S., De Bellis, F., and Altucci, L., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 2530.CrossRefGoogle Scholar
  25. 25.
    Suganthi, R., Lakshmi, S.S., Kannappan, G., and Rahuman, A.A., J. Pharm. Res., 2011, vol. 4, p. 4574.Google Scholar
  26. 26.
    Kosaka, W., Yamamoto, N., and Miyasaka, H., Inorg. Chem., 2013, vol. 52, p. 9908.CrossRefGoogle Scholar
  27. 27.
    Ravi Krishna, E., Muralidhar Reddy, P., Sarangapani, M., Hanmanthu, G., Geeta, B., Shoba Rani, K., and Ravinder, V., Spectrochim. Acta, Part A, 2012, vol. 97, p. 189.CrossRefGoogle Scholar
  28. 28.
    Pryadeina, M.V., Burgart, Ya.V., Saloutin, V.I., Slepukhin, P.A., Kazheva, O.N., Shilov, G.V., D’yachenko, O.A., and Chupakhin, O.N., Russ. J. Org. Chem., 2007, vol. 43, p. 945.CrossRefGoogle Scholar
  29. 29.
    Zahrt, T.C., Song, J., Siple, J., and Deretic, V., Mol. Microbiol., 2001, vol. 39, p. 1174.CrossRefGoogle Scholar
  30. 30.
    Khudina, O.G., Ivanova, A.E., Burgart, Ya.V., Saloutin, V.I., and Kravchenko, M.A., J. Fluorine Chem., 2013, vol. 147, p. 31.CrossRefGoogle Scholar
  31. 31.
    Vasilev, V.N., Mikobakteriozy i mikozy legkikh (Mycobacterioses and Lung Mycoses), Sofiya: Meditsina i Fizkul’tura, 1971, p. 377.Google Scholar
  32. 32.
    Palanki, M.S.S., Erdman, P.E., Gayo-Fung, L.M., Shevlin, G.I., Sullivan, R.W., Suto, M.J., Goldman, M.E., Ransone, L.J., Bennett, B.L., and Manning, A.M., J. Med. Chem., 2000, vol. 43, p. 3995.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  • Yu. S. Kudyakova
    • 1
  • Ya. V. Burgart
    • 1
  • V. I. Saloutin
    • 1
  1. 1.Postovskii Institute of Organic SynthesisUral Branch, Russian Academy of SciencesYekaterinburgRussia

Personalised recommendations