Skip to main content
SpringerLink
Log in

Synthesis of 1,4-dihydropyridines having an N-alkylpyridinium substituent at the 4-position and their affinity towards liposomal membranes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

There has been synthesized a series of 1,4-dihydropyridines having an N-alkylpyridinium substituent at position 4 with a varying length of hydrocarbon chain. Their affinity to model (liposomal) membranes has been studied. It was found that this affinity increased with lengthening of the hydrocarbon chain on the Npyridinium substituent at the 4-position of the 1,4-dihydropyridine ring. However, lengthening of the hydrocarbon chain in the 3,5-ester groups of the 1, 4-dihydropyridine ring led to a decrease in the binding to the liposome when a 4-(N-hexadecylpyridinium) substituent was present.

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. D. J. Triggle, J. Cardiovascular Pharmacol.,18, S1 (1991).

    Google Scholar 

  2. K. Kiue and T. Sano, Cancer Res.,50, 310 (1990).

    PubMed  Google Scholar 

  3. E. Ivanov, T. Ponomarova, G. Merkusev, G. Dubur, É. Bisenieks, A. Dauvarte, and E. Pilscik, Radiobiol. Radiotherm.,31, 69 (1990).

    Google Scholar 

  4. J. Poikans, G. Tirzitis, E. Bisenieks, J. Uldrikis, V. Gurevich, I. Mikhailova, and G. Duburs, Eur. J. Med. Chem.,29, 325 (1994).

    Google Scholar 

  5. R. P. Mason, Biochem. Pharmacol.,45, 2173 (1993).

    PubMed  Google Scholar 

  6. N. V. Makarova, G. V. Belevich, É. A. Bisenieks, M. M. Veveris, and G. Ya. Dubur, Khim.-farm. Zh., No. 7, 810 (1988).

  7. N. Baindur, A. Rutledge, and D. Triggle, J. Med. Chem.,36, 3743 (1993).

    PubMed  Google Scholar 

  8. R. P. Mason, G. E. Gonye, D. W. Chester, and L. G. Herbette, Biophys. J.,55, 769 (1989).

    PubMed  Google Scholar 

  9. R. P. Mason, D. G. Rhodes, and L. G. Herbette, J. Med. Chem.,34, 869 (1991).

    PubMed  Google Scholar 

  10. H. D. Bauerle and J. Seelig, Biochemistry,30, 7203 (1991).

    PubMed  Google Scholar 

  11. Yu. A. Vladimirov and G. E. Dobretsov, Fluorescence Probes and Investigation of Biological Membranes [in Russian], Nauka, Moscow (1980), p. 320.

    Google Scholar 

  12. J. Lakovich, Basic Fluorescence Spectroscopy [Russian translation], Mir, Moscow (1986), p. 496.

    Google Scholar 

Download references

Authors
  1. N. V. Makarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zh. V. Koronova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Plotnietse
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. Ya. Tirzite
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. D. Tirzit
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. Ya. Duburs
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Latvian Institute of Organic Synthesis, Riga LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1112–1117, August, 1995. Original article submitted June 6, 1995.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Makarova, N.V., Koronova, Z.V., Plotnietse, A.V. et al. Synthesis of 1,4-dihydropyridines having an N-alkylpyridinium substituent at the 4-position and their affinity towards liposomal membranes. Chem Heterocycl Compd 31, 969–973 (1995). https://doi.org/10.1007/BF01170324

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01170324

Keywords

Search

Navigation