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Russian Journal of Organic Chemistry

, Volume 54, Issue 10, pp 1498–1504 | Cite as

Synthesis of Allocolchicine Conjugates with a Cetirizine Analog

  • A. S. Zotov
  • E. S. Shchegravina
  • A. Yu. FedorovEmail author
Article
  • 12 Downloads

Abstract

Conjugates of allocolchicine and a cetirizine analog have been synthesized as potential anti-inflammatory and anti-allergic drugs.

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References

  1. 1.
    Pawankar, R., Canonica, G.W., Holgate, S.T., and Lockey, R.F., Belaya kniga WAO po allergii 2011–2012 (WAO White Book on Allergy 2011–2012), Moscow: Meditsina-Zdorov’e, 2011, p. 12.Google Scholar
  2. 2.
    Passalacqua, G., Canonica, G.W., and Bousquet, J., Clin. Allergy Immunol., 2002, vol. 17, p. 65.Google Scholar
  3. 3.
    Vena, G.A., Cassano, N., Buquicchio, R., and Ventura, M.T., Curr. Pharm. Des., 2008, vol. 14, no. 27, p. 2902.CrossRefGoogle Scholar
  4. 4.
    Simons, F.E.R., N. Engl. J. Med., 2004, vol. 351, no. 21, p. 2203.CrossRefGoogle Scholar
  5. 5.
    Sharma, A. and Hamelin, B.A., Curr. Drug Metab., 2003, vol. 4, no. 2, p. 105.CrossRefGoogle Scholar
  6. 6.
    Kalpaklioglu, F. and Baccioglu, A., Anti-Inflammatory Anti-Allergy Agents Med. Chem., 2012, vol. 11, no. 3, p. 230.CrossRefGoogle Scholar
  7. 7.
    Simons, F., Estelle, R., and Simons, K.J., J. Allergy Clin. Immunol., 2011, vol. 128, no. 6, p. 1139.CrossRefGoogle Scholar
  8. 8.
    Thurmond, R.L., Gelfand, E.W., and Dunford, P.J., Nat. Rev. Drug Discovery, 2008, vol. 7, no. 1, p. 41.CrossRefGoogle Scholar
  9. 9.
    Beaton, G. and Moree, W.J., Expert Opin. Ther. Pat., 2010, vol. 20, no. 9, p. 1197.CrossRefGoogle Scholar
  10. 10.
    Mahdy, A.M. and Webster, N.R., Anaesth. Int. Care Med., 2017, vol. 18, no. 4, p. 210.CrossRefGoogle Scholar
  11. 11.
    Leurs, R., Church, M.K., and Taglialatela, M., Clin. Exp. Allergy, 2002, vol. 32, no. 4, p. 489.CrossRefGoogle Scholar
  12. 12.
    DuBuske, L.M., Clin. Ther., 1999, vol. 21, p. 281.CrossRefGoogle Scholar
  13. 13.
    Wellington, K. and Jarvis, B., Drugs, 2001, vol. 61, p. 2231.CrossRefGoogle Scholar
  14. 14.
    Schwender, C.F., Beers, S.A., Malloy, E.A., and Cinicola, J., Bioorg. Med. Chem. Lett., 1996, vol. 6, p. 311.CrossRefGoogle Scholar
  15. 15.
    Milani, C., Carminati, G.M., and Sovera, A., GB Patent no. 2 076 403, 1981.Google Scholar
  16. 16.
    Cossement, E., Gobert, J., and Bodson, G., GB Patent no. 2 225 320, 1990.Google Scholar
  17. 17.
    Boye O., Brossi A., The Alkaloids: Chemistry and Pharmacology, Brossi, A. and Cordell, G.A., Eds., San Diego: Academic, 1992, vol. 41, p. 125.Google Scholar
  18. 18.
    Finkelstein, Y., Aks, S.E., Hutson, J.R., Juurlink, D.N., Nguyen, P., Dubnov-Raz, G., Pollak, U., Koren, G., and Bentur, Y., Clin. Toxicol., 2010, vol. 48, p. 407.CrossRefGoogle Scholar
  19. 19.
    Cronstein, B.N., Molad, Y., Reibman, J., Balakhane, E., Levin, R.I., and Weissmann, G., J. Clin. Invest., 1995, vol. 96, p. 994.CrossRefGoogle Scholar
  20. 20.
    Pope, R.M. and Tschopp, J., Arthritis Rheum., 2007, vol. 56, p. 3183.CrossRefGoogle Scholar
  21. 21.
    Martinon, F., Petrilli, V., Mayor, A., Tardivel, A., and Tschopp, J., Nature, 2006, vol. 440, p. 237.CrossRefGoogle Scholar
  22. 22.
    Machhindra, G., Fazlur-Rahman, N.K., Amit, K., and Varadhan, K., Eur. J. Pharm. Sci., 2013, vol. 49, p. 227.CrossRefGoogle Scholar
  23. 23.
    Gazal, G. and Mackie, I.C., Int. J. Paediatr. Dent., 2007, vol. 17, p. 169.CrossRefGoogle Scholar
  24. 24.
    Bhattacharyya, B., Panda, D., Gupta, S., and Banerjee, M., Med. Res. Rev., 2008, vol. 28, no. 1, p. 155.CrossRefGoogle Scholar
  25. 25.
    Sitnikov, N.S. and Fedorov, A.Yu., Russ. Chem. Rev., 2013, vol. 82, no. 5, p. 393.CrossRefGoogle Scholar
  26. 26.
    Sitnikov, N.S., Velder, J., Abodo, L., Cuvelier, N., Neudorfl, J., Prokop, A., Krause, G., Fedorov, A.Yu., and Schmalz, H.-G., Chem. Eur. J., 2012, vol. 18, p. 12 096.CrossRefGoogle Scholar
  27. 27.
    Malysheva, Yu.B., Combes, S., Knochel, P., Gavrushin, A.E., and Fedorov, A.Yu., Bioorg. Med. Chem., 2012, vol. 20, p. 4271.CrossRefGoogle Scholar
  28. 28.
    Kuznetsova, N.R., Svirshevskaya, E.V., Sitnikov, N.S., Abodo, L., Sutorius, H., Zapke, J., Velder, J., Tomopoulou, P., Oschkinat, H., Prokop, A., Schmalz, H.-G., Fedorov, A.Yu., and Vodovozova, E.L., Russ. J. Bioorg. Chem., 2013, vol. 39, no. 5, p. 543.CrossRefGoogle Scholar
  29. 29.
    Sitnikov, N.S., Kokisheva, A.S., Fukin, G.K., Neudörfl, J.-M., Sutorius, H., Prokop, A., Fokin, V.V., Schmalz, H.-G., and Fedorov, A.Yu., Eur. J. Org. Chem., 2014, p. 6481.Google Scholar
  30. 30.
    Voitovich, Yu.V., Schegravina, E.S., Sitnikov, N.S., Faerman, V.I., Fokin, V.V., Schmalz, H.-G., Combes, S., Allegro, D., Barbier, P., Beletskaya, I.P., Svirshchevskaya, E.V., and Fedorov, A.Yu., J. Med. Chem., 2015, vol. 58, p. 692.CrossRefGoogle Scholar
  31. 31.
    Schegravina, E.S., Knyazev, D., Svirshevskaya, E.V., Beletskaya, I.P., Schmalz, H.-G., and Fedorov, A.Yu., Eur. J. Org. Chem., 2016, vol. 34, p. 5620.CrossRefGoogle Scholar
  32. 32.
    Shchegravina, E.S., Maleev, A.A., Ignatov, S.K., Gracheva, I.A., Stein, A., Schmalz, H.-G., Gavryushin, A.E., Zubareva, A.A., Svirshchevskaya, E.V., and Fedorov, A.Yu., Eur. J. Med. Chem., 2017, vol. 141, p. 51CrossRefGoogle Scholar
  33. 33.
    Gracheva, I.A., Voitovich, I.V., Faerman, V.I., Sitnikov, N.S., Myrsikova, E.V., Schmalz, H.-G., Svirshchevskaya, E.V., and Fedorov, A.Yu., Eur. J. Med. Chem., 2017, vol. 126, p. 432.CrossRefGoogle Scholar
  34. 34.
    Konovalov, A.I., Antipin, I.S., Burilov, V.A., Madzhidov, T.I., Kurbangalieva, A.R., Nemtarev, A.V., Solovieva, S.E., Stoikov, I.I., Mamedov, V.A., Zakharova, L.Ya., Gavrilova, E.L., Sinyashin, O.G., Balova, I.A., Vasilyev, A.V., Zenkevich, I.G., Krasavin, M.Yu., Kuznetsov, M.A., Molchanov, A.P., Novikov, M.S., Nikolaev, V.A., Rodina, L.L., Khlebnikov, A.F., Beletskaya, I.P., Vatsadze, S.Z., Gromov, S.P., Zyk, N.V., Lebedev, A.T., Lemenovskii, D.A., Petrosyan, V.S., Nenaidenko, V.G., Negrebetskii, V.V., Baukov, Yu.I., Shmigol’, T.A., Korlyukov, A.A., Tikhomirov, A.S., Shchekotikhin, A.E., Traven’, V.F., Voskresenskii, L.G., Zubkov, F.I., Golubchikov, O.A., Semeikin, A.S., Berezin, D.B., Stuzhin, P.A., Filimonov, V.D., Krasnokutskaya, E.A., Fedorov, A.Yu., Nyuchev, A.V., Orlov, V.Yu., Begunov, R.S., Rusakov, A.I., Kolobov, A.V., Kofanov, E.R., Fedotova, O.V., Egorova, A.Yu., Charushin, V.N., Chupakhin, O.N., Klimochkin, Yu.N., Osyanin, V.A., Reznikov, A.N., Fisyuk, A.S., Sagitullina, G.P., Aksenov, A.V., Aksenov, N.A., Grachev, M.K., Maslennikova, V.I., Koroteev, M.P., Brel’, A.K., Lisina, S.V., Medvedeva, S.M., Shikhaliev, Kh.S., Suboch, G.A., Tovbis, M.S., Mironovich, L.M., Ivanov, S.M., Kurbatov, S.V., Kletskii, M.E., Burov, O.N., Kobrakov, K.I., and Kuznetsov, D.N., Russ. J. Org. Chem., 2018, vol. 54, no. 2, p. 157.CrossRefGoogle Scholar
  35. 35.
    Antipin, I.S., Kazymova, M.A., Kuznetsov, M.A., Vasilyev, A.V., Ishchenko, M.A., Kiryushkin, A.A., Kuznetsova, L.M., Makarenko, S.V., Ostrovskii, V.A., Petrov, M.L., Solod, O.V., Trishin, Yu.G., Yakovlev, I.P., Nenaidenko, V.G., Beloglazkina, E.K., Beletskaya, I.P., Ustynyuk, Yu.A., Solov’ev, P.A., Ivanov, I.V., Malina, E.V., Sivova, N.V., Negrebetskii, V.V., Baukov, Yu.I., Pozharskaya, N.A., Traven’, V.F., Shchekotikhin, A.E., Varlamov, A.V., Borisova, T.N., Lesina, Yu.A., Krasnokutskaya, E.A., Rogozhnikov, S.I., Shurov, S.N., Kustova, T.P., Klyuev, M.V., Khelevina, O.G., Stuzhin, P.A., Fedorov, A.Yu., Gushchin, A.V., Dodonov, V.A., Kolobov, A.V., Plakhtinskii, V.V., Orlov, V.Yu., Kriven’ko, A.P., Fedotova, O.V., Pchelintseva, N.V., Charushin, V.N., Chupakhin, O.N., Klimochkin, Yu.N., Klimochkina, A.Yu., Kuryatnikov, V.N., Malinovskaya, Yu.A., Levina, A.S., Zhuravlev, O.E., Voronchikhina, L.I., Fisyuk, A.S., Aksenov, A.V., Aksenov, N.A., and Aksenova, I.V., Russ. J. Org. Chem., 2017, vol. 53, no. 9, p. 1275.CrossRefGoogle Scholar
  36. 36.
    Crielaard, B.J., van der Wal, S., Le, H.T., Bode, A.T.L., Lammers, T., Hennink, W.E., Schiffelers, R.M., Fens, M.H.A.M., and Storm, G., Eur. J. Pharm. Sci., 2012, vol. 45, p. 429.CrossRefGoogle Scholar
  37. 37.
    Nicolas, N., Reball, J., Sitnikov, N., Velder, J., Termath, A., Fedorov, A.Yu., and Schmalz, H.-G., Heterocycles, 2011, vol. 82, p. 1585.Google Scholar
  38. 38.
    Li, J.J., Johnson, D.S., Sliskovic, D.R., and Roth, B.D., Contemporary Drug Synthesis, Hoboken: Wiley, 2004, p. 48CrossRefGoogle Scholar
  39. 39.
    Nemeckova-Herova, D. and Pazdera, P., Curr. Org. Synth., 2015, vol. 12, p. 173.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • A. S. Zotov
    • 1
  • E. S. Shchegravina
    • 1
  • A. Yu. Fedorov
    • 1
    Email author
  1. 1.Lobachevskii National Research State University of Nizhny NovgorodNizhny NovgorodRussia

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