Skip to main content
SpringerLink
Log in

N-[4-(arylpiperazin-1-yl)butyl]bicyclo[2.2.1]hept-5-ene-endo-2,endo-3-dicarboximides and Their Epoxy Derivatives. Synthesis and affinity for 5-HT1a receptors

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

New ligands for 5-HT1A serotonin receptors, N-[4-(4-arylpiperazin-1-yl)butyl]bicyclo[2.2.1]hept-5-ene-endo-2,endo-3-dicarboximides and their epoxy derivatives, were synthesized, and their affinity for 5-HT1A receptors was estimated at 16.2 ± 2.0 to 0.60 ± 0.08 nM.

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

Similar content being viewed by others

References

  1. Wu, Y.H., Smith, K.R., Rayburn, J.W., and Kissel, J.W., J. Med. Chem., 1969, vol. 12, no. 5, p. 876.

    Article  CAS  Google Scholar 

  2. Lopez-Rodriguez, M.L., Ayala, D., Benhamu, B., Morcillo, M.J., and Viso, A., Curr. Med. Chem., 2002, vol. 9, p. 443.

    CAS  Google Scholar 

  3. Andronati, S.A. and Makan, S.Yu., Azotistye geterotsikly i alkaloidy (Nitrogen-Containing Heterocycles and Alkaloids), Moscow: Iridium, 2001, vol. 1, p. 30.

    Google Scholar 

  4. Glennon, R.A., Drug Dev. Res., 1992, vol. 26, p. 251

    Article  CAS  Google Scholar 

  5. Caliendo, G., Santagada, V., Perissutti, E., and Fiorino, F., Curr. Med. Chem., 2005, vol. 12, no. 15, p. 1721.

    Article  CAS  Google Scholar 

  6. Den Boer, J.A., Bosker, F.J., and Slaap, B.R., Hum. Psychopharmacol., 2000, vol. 15, p. 315

    Article  Google Scholar 

  7. Jordan, S., Koprivica, V., Chen, R., Tottori, K., Kikuchi, T., and Altar, C.A., Eur. J. Pharmacol., 2002, vol. 441, p. 137.

    Article  CAS  Google Scholar 

  8. Tunnicliff, G., Pharmacol. Toxicol., 1991, vol. 69, p. 149.

    Article  CAS  Google Scholar 

  9. Barradell, L.B. and Fitton, A., CNS Drugs, 1996, vol. 5, no. 2, p. 147.

    Article  CAS  Google Scholar 

  10. Fiorino, F., Perissutti, E., Severino, B., Santagada, V., Cirillo, D., Terracciano, S., Massarelli, P., Bruni, G., Collavoli, E., Renner, C., and Caliendo, G., J. Med. Chem., 2005, vol. 48, p. 5495.

    Article  CAS  Google Scholar 

  11. Bronowska, A., Les, A., Chilmonczyk, Z., Filipek, S., Edvardsen, O., Ostensen, R., and Sylte, I., Bioorg. Med. Chem., 2001, vol. 9, p. 881.

    Article  CAS  Google Scholar 

  12. Strzelczyk, A.A., Jaronczyk, M., Chilmonczyk, Z., Mazurek, A.P., Chojnacka-Wojcik, E., and Sylte, I., Biochem. Pharmacol., 2004, vol. 67, p. 2219.

    Article  CAS  Google Scholar 

  13. Lopez-Rodriguez, M.L., Vicente, B., Deupi, X., Barrondo, S., Olivella, M., Morcillo, M.J., Behamu, B., Ballesteros, J.A., Salles, J., and Pardo, L., Mol. Pharmacol., 2002, vol. 62, p. 15.

    Article  CAS  Google Scholar 

  14. Lopez-Rodriguez, M.L., Morcillo, M.J., Fernandez, E., Benhamu, B., Tejada, I., Ayala, D., Viso, A., Campillo, M., Pardo, L., Delgado, M., Manzanares, J., and Fuentes, J.A., J. Med. Chem., 2005, vol. 48, p. 2548.

    Article  CAS  Google Scholar 

  15. Nowak, M., Kolaczkowski, M., Pawlowski, M., and Bojarski, A.J., J. Med. Chem., 2006, vol. 49, p. 205.

    Article  CAS  Google Scholar 

  16. JPN Patent Appl. no. 63-132 887, 1988; Ref. Zh., Khim., 1990, no. 7 O 108.

  17. US Patent no. 5 011 841, 1991; Ref. Zh., Khim., 1992, no. 9 O 245.

  18. JPN Patent Appl. no. 228 153, 1990; Ref. Zh., Khim., 1992, no. 12 O 111.

  19. ChSSR Patent no. 251 992, 1988; Ref. Zh., Khim., 1989, no. 10 O 153.

  20. Tarabara, I.N., Zlenko, E.T., Bondarenko, Ya.S., Krishchik, O.V., and Kas’yan, L.I., Zh. Org. Farm. Khim., 2006, vol. 4, no. 2, p. 54.

    CAS  Google Scholar 

  21. Zlenko, O.T., Kas’yan, L.I., Mamchur, V.I., Tarabara, I.N., Bondarenko, Ya.S., and Oprishko, V.I., Ukrainian Patent no. 20 676, 2006; Byull. Izobret., 2007, no. 2.

  22. Tarabara, I.N., Kas’yan, A.O., Krishchik, O.V., Shishkina, S.V., Shishkin, O.V., and Kas’yan, L.I., Russ. J. Org. Chem., 2002, vol. 38, no. 9, p. 1299.

    Article  CAS  Google Scholar 

  23. Kas’yan, L.I., Krishchik, O.V., Umrykhina, L.K., and Kas’yan, A.O., Visn. Dnipropetr. Univ., Khim., 1998, no. 3, p. 87.

  24. Andronati, S.A., Makan, S.Yu., Kolodeev, G.E., and Berezhnoi, D.S., Khim.-Farm. Zh., 2001, vol. 35, no. 11, p. 11.

    Google Scholar 

  25. Cheng, Y.C. and Prusoff, W.H., Biochem. Pharmacol., 1973, vol. 22, no. 23, p. 3099.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, Lyustdorfskaya dor. 86, Odessa, 65080, Ukraine

    S. Yu. Makan, D. I. Tsymbal & S. A. Andronati

  2. Mechnikov Odessa National University, Odessa, Ukraine

    S. G. Soboleva

  3. Dnepropetrovsk National University, Dnepropetrovsk, Ukraine

    I. N. Tarabara & L. I. Kas’yan

Authors
  1. S. Yu. Makan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. I. Tsymbal
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. G. Soboleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. N. Tarabara
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. I. Kas’yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. A. Andronati
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. I. Tsymbal.

Additional information

Original Russian Text © S.Yu. Makan, D.I. Tsymbal, S.G. Soboleva, I.N. Tarabara, L.I. Kas’yan, S.A. Andronati, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 2, pp. 303–307.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Makan, S.Y., Tsymbal, D.I., Soboleva, S.G. et al. N-[4-(arylpiperazin-1-yl)butyl]bicyclo[2.2.1]hept-5-ene-endo-2,endo-3-dicarboximides and Their Epoxy Derivatives. Synthesis and affinity for 5-HT1a receptors. Russ J Gen Chem 79, 292–296 (2009). https://doi.org/10.1134/S1070363209020212

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363209020212

Keywords

Search

Navigation