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Medicinal Chemistry Research

, Volume 28, Issue 5, pp 742–753 | Cite as

Synthesis of new 1-benzyl tetrahydropyridin-4-ylidene piperidinium salts and their antiplasmodial and antitrypanosomal activities

  • Noor-ul-Amin Mohsin
  • Werner SeebacherEmail author
  • Patrick Hochegger
  • Johanna Faist
  • Robert Saf
  • Marcel Kaiser
  • Pascal Mäser
  • Robert Weis
Original Research
  • 87 Downloads

Abstract

Our last study revealed the distinct antiplasmodial and antitrypanosomal activities of 1-benzyl tetrahydropyridin-4-ylidene pyrrolidinium salts. Therefore, we prepared a series of new 1-benzyl tetrahydropyridin-4-ylidene ammonium salts with an alternative amino residue and varying substitution patterns at the benzyl group to investigate the influence of these modifications on the biological activities. All new compounds were characterized by spectroscopic methods like ultraviolet, infrared, nuclear magnetic resonance, as well as high- resolution mass spectra. They were tested for their activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense as well as for their cytotoxicity against L6 cells using microplate assays. The results show that the structure of the amino residue as well as the substitution pattern of the benzyl group influences the biological activities distinctly. Physicochemical parameters are calculated and structure–activity relationships are discussed.

Keywords

1-benzyl tetrahydropyridin-4-ylidene ammonium salts Antiplasmodial activity Antitrypanosomal activity Structure–activity relationships 

Notes

Compliance with ethical standards

Conflict of interests

The authors declare that they have no conflict of interest.

Ethical approval

All protocols and procedures used in both in vivo studies were reviewed and approved by the local veterinary authorities of the Canton Basel-Stadt.

Supplementary material

44_2019_2331_MOESM1_ESM.docx (9.2 mb)
Supplementary Information

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Faculty of Pharmaceutical sciencesGovernment College UniversityFaisalabadPakistan
  2. 2.Institute of Pharmaceutical Sciences, Pharmaceutical ChemistryUniversity of GrazGrazAustria
  3. 3.Institute for Chemistry and Technology of Organic Materials (ICTM)Graz University of TechnologyGrazAustria
  4. 4.Swiss Tropical and Public Health InstituteBaselSwitzerland
  5. 5.University of BaselBaselSwitzerland

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