Preparation of new 1,3-dibenzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities

New 1,3 dibenzyl -tetrahydropyridinylidene ammonium salts have been prepared from unsubstituted or N-benzylated tetrahydropyridinylidene ammonium salts. The antiplasmodial and antitrypanosomal activities as well as their cytotoxic effects were determined using microplate assays. In addition, their a...

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Veröffentlicht in:European journal of medicinal chemistry 2021-01, Vol.210, p.112969, Article 112969
Hauptverfasser: Petritsch, Markus, Seebacher, Werner, Mohsin, Noor-ul-Amin, Dolensky, Johanna, Hochegger, Patrick, Kaiser, Marcel, Mäser, Pascal, Belaj, Ferdinand, Saf, Robert, Kretschmer, Nadine, Alajlani, Muaaz, Brantner, Adelheid, Bauer, Rudolf, Schühly, Wolfgang, Weis, Robert
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Sprache:eng
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Zusammenfassung:New 1,3 dibenzyl -tetrahydropyridinylidene ammonium salts have been prepared from unsubstituted or N-benzylated tetrahydropyridinylidene ammonium salts. The antiplasmodial and antitrypanosomal activities as well as their cytotoxic effects were determined using microplate assays. In addition, their activities against two gram positive and two gram negative bacteria strains and a yeast strain were examined. Furthermore, anticancer effects against two cell lines were investigated. Physicochemical parameters were calculated and structure-activity-relationships discussed. One compound showed antiplasmodial activity against a multiresistant strain of Plasmodium falciparum in subnanomolar concentration. Antitrypanosomal activities were detected in low nanomolar concentrations. A single compound was active against grampositive and gramnegative bacteria, as well as yeast. One compound inhibited the growth of a HCT cell line in low concentration. [Display omitted] •New N-dibenzyltetrahydropyridinylideneammonium salts were prepared and characterized.•Their antiprotozoal, antibacterial and anticancer activities were investigated.•Physicochemical parameters and structure-activity relationships are described.•A compound is in vitro more active against a multiresistant strain than artemisinin.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2020.112969