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

Markus Petritsch; Werner Seebacher; Noor ul Amin Mohsin; Johanna Dolensky; Patrick Hochegger; Marcel Kaiser; Pascal Mäser; Ferdinand Belaj; Robert Saf; Nadine Kretschmer; Muaaz Alajlani; Adelheid Brantner; Rudolf Bauer; Wolfgang Schühly; Robert Weis

doi:10.1016/j.ejmech.2020.112969

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

Markus Petritsch, Werner Seebacher^*, Noor ul Amin Mohsin, Johanna Dolensky, Patrick Hochegger, Marcel Kaiser, Pascal Mäser, Ferdinand Belaj, Robert Saf, Nadine Kretschmer, Muaaz Alajlani, Adelheid Brantner, Rudolf Bauer, Wolfgang Schühly, Robert Weis

^*Corresponding author for this work

Institute for Chemistry and Technology of Materials (6380)

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Article number	112969
Journal	European Journal of Medicinal Chemistry
Volume	210
DOIs	https://doi.org/10.1016/j.ejmech.2020.112969
Publication status	Published - 15 Jan 2021

Keywords

1,3 dibenzyl tetrahydropyridinylidene ammonium salts
Antibacterial
Anticancer
Antiplasmodial
Antitrypanosomal

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2020.112969

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Petritsch, M., Seebacher, W., Mohsin, N. U. A., Dolensky, J., Hochegger, P., Kaiser, M., Mäser, P., Belaj, F., Saf, R., Kretschmer, N., Alajlani, M., Brantner, A., Bauer, R., Schühly, W., & Weis, R. (2021). Preparation of new 1,3-dibenzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities. European Journal of Medicinal Chemistry, 210, Article 112969. https://doi.org/10.1016/j.ejmech.2020.112969

Petritsch, M, Seebacher, W, Mohsin, NUA, Dolensky, J, Hochegger, P, Kaiser, M, Mäser, P, Belaj, F, Saf, R, Kretschmer, N, Alajlani, M, Brantner, A, Bauer, R, Schühly, W & Weis, R 2021, 'Preparation of new 1,3-dibenzyl tetrahydropyridinylidene ammonium salts and their antimicrobial and anticellular activities', European Journal of Medicinal Chemistry, vol. 210, 112969. https://doi.org/10.1016/j.ejmech.2020.112969

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abstract = "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.",

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AU - Dolensky, Johanna

AU - Hochegger, Patrick

AU - Kaiser, Marcel

AU - Mäser, Pascal

AU - Belaj, Ferdinand

AU - Saf, Robert

AU - Kretschmer, Nadine

AU - Alajlani, Muaaz

AU - Brantner, Adelheid

AU - Bauer, Rudolf

AU - Schühly, Wolfgang

AU - Weis, Robert

PY - 2021/1/15

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N2 - 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.

AB - 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.

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KW - Anticancer

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KW - Antitrypanosomal

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

Abstract

Keywords

ASJC Scopus subject areas

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