Skip to main content
SpringerLink
Log in

Modification of the anticestodal drug 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide with a view to improve its biological effect

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

Abstract

Reactions of 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide, the active substance of the drug Niclosamide (Phenasal), with higher amines (dodecan-1-amine, hexadecan-1-amine) and 1-(2-aminoethyl)-piperazine lead to the formation of the corresponding water-soluble ammonium salts with retention of pharmacophoric groups responsible for the antihelminthic effect, whereas no nucleophilic aromatic substitution of chlorine is observed. The product structure was determined by X-ray analysis.

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. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2010, 16th ed., vol. 2, p. 370.

    Google Scholar 

  2. Caira, M.R., J. Inclusion Phenom., 1998, vol. 31, p. 27.

    Article  Google Scholar 

  3. Cambridge Structural Database System. Version 5, 2013, p. 34.

  4. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2010, 16th ed., vol. 2, p. 366.

    Google Scholar 

  5. Armagero, W.L.F. and Li Lin Chai, C., Purification of Laboratory Chemicals, Amsterdam: Elsevier, 2009, 6th ed.

    Google Scholar 

  6. Sheldrick, G.M., SADABS. Program for Absorption Corrections, Göttingen, Germany: Univ. Göttingen, 1996.

    Google Scholar 

  7. Sheldrick, G.M., SHELXL-97 Program for Crystal Structure Refinement, Göttingen, Germany: Univ. of Göttingen, 1996.

    Google Scholar 

  8. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837.

    Article  CAS  Google Scholar 

  9. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A). Bruker Advanced X-Ray Solutions, Madison, Wisconsin, USA: Bruker AXS, 2006.

  10. Macrae, F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., and van de Streek, J., J. Appl. Crystallogr., 2006, vol. 39, p. 453.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Kazan (Volga Region) Federal University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia

    I. V. Galkina, D. R. Chubukaeva, Yu. V. Bakhtiyarova, V. I. Galkin, R. A. Cherkasov & D. R. Islamov

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    O. N. Kataeva

Authors
  1. I. V. Galkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. R. Chubukaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. V. Bakhtiyarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. I. Galkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. R. A. Cherkasov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. D. R. Islamov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. O. N. Kataeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Galkina.

Additional information

Dedicated to Full Member of the Russian Academy of Sciences O.N. Chupakhin on his 80th anniversary

Original Russian Text © I.V. Galkina, D.R. Chubukaeva, Yu.V. Bakhtiyarova, V.I. Galkin, R.A. Cherkasov, D.R. Islamov, and O.N. Kataeva, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 6, pp. 818–822.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Galkina, I.V., Chubukaeva, D.R., Bakhtiyarova, Y.V. et al. Modification of the anticestodal drug 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide with a view to improve its biological effect. Russ J Org Chem 50, 800–804 (2014). https://doi.org/10.1134/S1070428014060074

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014060074

Keywords

Search

Navigation