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Synthesis of 3-alkoxycarbonyl-6-alkylsulfanyl-4-[2-(difluoromethoxy)phenyl]-1,4-dihydropyridines and related derivatives as analogs of cognition enhancer cerebrocrast

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Chemistry of Heterocyclic Compounds Aims and scope

4-[2-(Difluoromethoxy)phenyl]-substituted 3-alkoxycarbonyl-6-alkylsulfanyl-3-cyano-2-methyl-1,4-di-hydropyridines and related pyridine and 4,7-dihydrothieno[2,3-b]pyridine derivatives have been prepared, their memory-improving activity has been studied using the passive avoidance responses in the acquisition test, and their calcium overload-preventing activity in SH-SY5Y neuroblastoma cell line in the presence of the agonist carbachol has been examined. 1,4-Dihydropyridine derivatives bearing the 2-propoxyethoxycarbonyl group in position 3 and having weak influence on calcium overload in neuronal cells show high activity comparable with that of cerebrocrast.

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References

  1. D. J. Triggle, Mini-Rev. Med. Chem., 3, 215 (2003).

    Article  CAS  Google Scholar 

  2. R. P. Mason, P. Marche, and T. H. Hintze, Arterioscler. Thromb. Vasc. Biol., 23, 2155 (2003).

    Article  CAS  Google Scholar 

  3. R. Vitolina, A. Krauze, G. Duburs, and A.Velena, Int. J. Pharm. Sci. Res., 3, 942 (2012).

    Google Scholar 

  4. S. Yamagishi, K. Nakamura, K. Takenaka, T. Matsui, and H. Inoue, Curr. Pharm. Des., 12, 1543 (2006).

    Article  CAS  Google Scholar 

  5. G. Duburs, B. Vigante, A. Plotniece, A. Krauze, A. Sobolevs, J. Briede, V. Klusa, and A. Velena, Chim. Oggi, 28, 68 (2008).

    Google Scholar 

  6. M. A. S. Fernandes, M. S. Santos, A. J. M. Moreno, L. Chernova, A. Krauze, G. Duburs, and J. A. F. Vicente, Toxicol. In Vitro, 23, 1333 (2009).

    Article  CAS  Google Scholar 

  7. V. Lukic-Panin, T. Kamiya, H. Zhang, T. Hayashi, A. Tsuchiya, Y. Sehara, K. Deguchi, T. Yamashita, and K. Abe, Brain Res., 1176, 143 (2007).

    Article  CAS  Google Scholar 

  8. E. Ilijic, J. N. Guzman, and D. J. Surmeier, Neurobiol. Dis., 43, 364 (2011).

    Article  CAS  Google Scholar 

  9. R. Leon, R. C. de Los, J. Marco-Contelles, M. G. Lopez, A. G. Garcia, and M. Villarroya, Eur. J. Med. Chem., 43, 668 (2008).

    Article  CAS  Google Scholar 

  10. R. Vilskersts, B. Vigante, Z. Neidere, A. Krauze, I. Domracheva, L. Bekere, I. Shestakova, G. Duburs, and M. Dambrova, Lett. Drug Des. Discovery, 9, 322 (2012).

    Article  CAS  Google Scholar 

  11. A. Krauze, R. O. Vitolina, M. R. Romanova, and G. Ya. Dubur, Khim.-Farm. Zh., 22, 548 (1988). [Pharm. Chem. J., 22, 366 (1991)].

    CAS  Google Scholar 

  12. Krauze, L. Baumane, L. Sile, L. Cherniva, M. Vilums, R. Vitolona, G. Duburs, and J. Stradins, Khim. Geterotsikl. Soedin., 1022 (2004). [Chem. Heterocycl. Compd., 40, 876 (2004)].

    Google Scholar 

  13. A. Krauze, A. G. Odinecs, A. A. Verreva, S. K. Germane, A. N. Kozhukov, and G. J. Dubur, Khim.-Farm. Zh., 25, 40 (1991). [Pharm. Chem. J., 25, 477 (1991).]

    CAS  Google Scholar 

  14. E. Kirule, A. A. Krauze, A. H. Velena, D. J. Antipova, G. J. Arnicane, and I. A. Vucina, Khim.-Farm. Zh., 26, 59 (1992). [Pharm. Chem. J., 26, 411 (1992).]

    CAS  Google Scholar 

  15. D. Tirzite, A. Krauze, A. Zubareva, G. Tirzits, and G. Duburs, Khim. Geterotsikl. Soedin., 902 (2002). [Chem. Heterocycl. Compd., 38, 795 (2002)].

    Google Scholar 

  16. G. J. Dubur, M. M. Veveris, G. Weinheimer, E. A. Bisenieks, N. R. Makarova, A. A. Kimenis, J. R. Uldrikis, E. J. Lukevics, D. Dooley, and H. Osswald, Arzneim. Forsch., 39, 1185 (1989).

    CAS  Google Scholar 

  17. G. Dubur, E. Bisenieks, S. Germane, V. Klusa, E. Bleidelis, and I. Misane, Eur. Pat. Appl. EP 499983.

  18. V. Klusa, Drug Future, 20, 135 (1995).

    Google Scholar 

  19. M. Drigelova, B. Tarabova, G. Duburs, and L. Lacinova, Can. J. Physiol. Pharmacol., 87, 923 (2009).

    Article  CAS  Google Scholar 

  20. Z. Andzans, A. Krauze, I. Adlere, L. Krasnova, and G. Duburs, Khim. Geterotsikl. Soedin., 454 (2013). [Chem. Heterocycl. Compd., 49, 421 (2013)].

    Google Scholar 

  21. S. K. Germane, O. E. Eberlinsh, and A. N. Kozhukov, in Scientific and Procedural Aspects of Biological Research on New Medicinal Drugs [in Russian], Zinatne, Riga (1987), p. 87.

    Google Scholar 

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Correspondence to Z. Andzans.

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*Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 607–614, April, 2012.

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Krauze, A., Andzans, Z., Krasnova, L. et al. Synthesis of 3-alkoxycarbonyl-6-alkylsulfanyl-4-[2-(difluoromethoxy)phenyl]-1,4-dihydropyridines and related derivatives as analogs of cognition enhancer cerebrocrast. Chem Heterocycl Comp 49, 566–573 (2013). https://doi.org/10.1007/s10593-013-1283-4

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