Synthesis of new 1-benzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities

Noor-Ul-Amin Mohsin; Werner Seebacher; Johanna Faist; Patrick Hochegger; Marcel Kaiser; Pascal Mäser; Ferdinand Belaj; Robert Saf; Nadine Kretschmer; Muaaz Alajlani; Ivana Turek; Adelheid Brantner; Rudolf Bauer; Franz Bucar; Robert Weis

doi:10.1016/j.ejmech.2017.11.025

Synthesis of new 1-benzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities

Eur J Med Chem. 2018 Jan 1:143:97-106. doi: 10.1016/j.ejmech.2017.11.025. Epub 2017 Nov 10.

Authors

Affiliations

¹ Faculty of Pharmaceutical Sciences, Government College University, Allama Iqbal Road, 38000 Faisalabad, Pakistan; Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, Austria.
² Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, Austria. Electronic address: we.seebacher@uni-graz.at.
³ Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, Austria.
⁴ Swiss Tropical and Public Health Institute, Socinstrasse 57, 4002 Basel, Switzerland; University of Basel, Petersplatz 1, 4003 Basel, Switzerland.
⁵ Institute of Chemistry, University of Graz, Universitätsplatz 1, 8010 Graz, Austria.
⁶ Institute for Chemistry and Technology of Organic Materials (ICTM), Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria.
⁷ Institute of Pharmaceutical Sciences, Pharmacognosy, University of Graz, Universitätsplatz 4, 8010 Graz, Austria.

PMID: 29172086
DOI: 10.1016/j.ejmech.2017.11.025

Abstract

A series of N-benzyl tetrahydropiperidinylidene pyrrolidinium salts have been synthesized and investigated for their antiplasmodial and antitrypanosomal activities as well as for their cytotoxic effects. The antibacterial, antimycobacterial and anticancer potencies of selected compounds were examined, too. Physicochemical parameters were calculated and structure-activity-relationships are discussed.

Keywords: Anticancer; Antimicrobial; Antiprotozoal; Benzyl tetrahydropiperidinylidene ammonium salts.

MeSH terms

Animals
Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Antifungal Agents / chemical synthesis
Antifungal Agents / chemistry
Antifungal Agents / pharmacology*
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Antiprotozoal Agents / chemical synthesis
Antiprotozoal Agents / chemistry
Antiprotozoal Agents / pharmacology*
Bacteria / drug effects
Benzyl Compounds / chemical synthesis
Benzyl Compounds / chemistry
Benzyl Compounds / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Mice
Microbial Sensitivity Tests
Molecular Structure
Parasitic Sensitivity Tests
Plasmodium falciparum / drug effects
Pyridines / chemical synthesis
Pyridines / chemistry
Pyridines / pharmacology*
Quaternary Ammonium Compounds / chemical synthesis
Quaternary Ammonium Compounds / chemistry
Quaternary Ammonium Compounds / pharmacology*
Rats
Saccharomyces cerevisiae / drug effects
Salts / chemical synthesis
Salts / chemistry
Salts / pharmacology
Structure-Activity Relationship
Trypanosoma brucei rhodesiense / drug effects

Substances

1-benzyl tetrahydropyridinylidene
Anti-Bacterial Agents
Antifungal Agents
Antineoplastic Agents
Antiprotozoal Agents
Benzyl Compounds
Pyridines
Quaternary Ammonium Compounds
Salts