Modifications and hybrids of 1,2,3,4-tetrahydropyridinium salts and their antiprotozoal potencies

Werner Seebacher; Noor ul Amin Mohsin; Johanna Dolensky; Patrick Hochegger; Marcel Kaiser; Pascal Mäser; Robert Saf; Daniela Schuster; Veronika Temml; Robert Weis

doi:10.1007/s00706-021-02847-y

Modifications and hybrids of 1,2,3,4-tetrahydropyridinium salts and their antiprotozoal potencies

Werner Seebacher^*, Noor ul Amin Mohsin, Johanna Dolensky, Patrick Hochegger, Marcel Kaiser, Pascal Mäser, Robert Saf, Daniela Schuster, Veronika Temml, Robert Weis

^*Corresponding author for this work

Institute for Chemistry and Technology of Materials (6380)

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

Abstract

The antiprotozoal activity of 1-benzyltetrahydropyridin-4-yliden iminium salts is reported. This paper describes the preparation of a series of analogs from dihydropyridines or dihydrothiopyrans as educts. The new compounds were investigated for their activity against Plasmodium falciparum NF54, a causative organism of Malaria tropica and Trypanosoma brucei rhodesiense, the causative organism of Human African Trypanosomiasis (sleeping sickness). Several structure–activity relationships were detected. Both the substituents in ring positions 1 and 4 of the tetrahydropyridinium moiety had a strong impact on the antiprotozoal activities as well as on the cytotoxicity of compounds against L-6 cells (rat skeletal myoblasts). All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. Graphic abstract: [Figure not available: see fulltext.].

Original language	English
Pages (from-to)	1347-1359
Number of pages	13
Journal	Monatshefte fur Chemie
Volume	152
Issue number	11
DOIs	https://doi.org/10.1007/s00706-021-02847-y
Publication status	Published - Nov 2021

Keywords

Antiprotozoal activity
Drug research
Heterocycles
Hybrids

ASJC Scopus subject areas

Chemistry(all)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/s00706-021-02847-yLicence: CC BY 4.0

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title = "Modifications and hybrids of 1,2,3,4-tetrahydropyridinium salts and their antiprotozoal potencies",

abstract = "The antiprotozoal activity of 1-benzyltetrahydropyridin-4-yliden iminium salts is reported. This paper describes the preparation of a series of analogs from dihydropyridines or dihydrothiopyrans as educts. The new compounds were investigated for their activity against Plasmodium falciparum NF54, a causative organism of Malaria tropica and Trypanosoma brucei rhodesiense, the causative organism of Human African Trypanosomiasis (sleeping sickness). Several structure–activity relationships were detected. Both the substituents in ring positions 1 and 4 of the tetrahydropyridinium moiety had a strong impact on the antiprotozoal activities as well as on the cytotoxicity of compounds against L-6 cells (rat skeletal myoblasts). All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. Graphic abstract: [Figure not available: see fulltext.].",

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year = "2021",

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doi = "10.1007/s00706-021-02847-y",

language = "English",

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T1 - Modifications and hybrids of 1,2,3,4-tetrahydropyridinium salts and their antiprotozoal potencies

AU - Seebacher, Werner

AU - Mohsin, Noor ul Amin

AU - Dolensky, Johanna

AU - Hochegger, Patrick

AU - Kaiser, Marcel

AU - Mäser, Pascal

AU - Saf, Robert

AU - Schuster, Daniela

AU - Temml, Veronika

AU - Weis, Robert

PY - 2021/11

Y1 - 2021/11

N2 - The antiprotozoal activity of 1-benzyltetrahydropyridin-4-yliden iminium salts is reported. This paper describes the preparation of a series of analogs from dihydropyridines or dihydrothiopyrans as educts. The new compounds were investigated for their activity against Plasmodium falciparum NF54, a causative organism of Malaria tropica and Trypanosoma brucei rhodesiense, the causative organism of Human African Trypanosomiasis (sleeping sickness). Several structure–activity relationships were detected. Both the substituents in ring positions 1 and 4 of the tetrahydropyridinium moiety had a strong impact on the antiprotozoal activities as well as on the cytotoxicity of compounds against L-6 cells (rat skeletal myoblasts). All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. Graphic abstract: [Figure not available: see fulltext.].

AB - The antiprotozoal activity of 1-benzyltetrahydropyridin-4-yliden iminium salts is reported. This paper describes the preparation of a series of analogs from dihydropyridines or dihydrothiopyrans as educts. The new compounds were investigated for their activity against Plasmodium falciparum NF54, a causative organism of Malaria tropica and Trypanosoma brucei rhodesiense, the causative organism of Human African Trypanosomiasis (sleeping sickness). Several structure–activity relationships were detected. Both the substituents in ring positions 1 and 4 of the tetrahydropyridinium moiety had a strong impact on the antiprotozoal activities as well as on the cytotoxicity of compounds against L-6 cells (rat skeletal myoblasts). All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. Graphic abstract: [Figure not available: see fulltext.].

KW - Antiprotozoal activity

KW - Drug research

KW - Heterocycles

KW - Hybrids

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DO - 10.1007/s00706-021-02847-y

M3 - Article

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SN - 0026-9247

VL - 152

SP - 1347

EP - 1359

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 11

ER -

Modifications and hybrids of 1,2,3,4-tetrahydropyridinium salts and their antiprotozoal potencies

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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