8-amino-6-methoxyquinoline—tetrazole hybrids: Impact of linkers on antiplasmodial activity

Patrick Hochegger; Johanna Dolensky; Werner Seebacher; Robert Saf; Marcel Kaiser; Pascal Mäser; Robert Weis

doi:10.3390/molecules26185530

8-amino-6-methoxyquinoline—tetrazole hybrids: Impact of linkers on antiplasmodial activity

Patrick Hochegger^*, Johanna Dolensky, Werner Seebacher, Robert Saf, Marcel Kaiser, Pascal Mäser, Robert Weis

^*Corresponding author for this work

Institute for Chemistry and Technology of Materials (6380)

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

Abstract

A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against Plasmodium falciparum NF54 as well as their cytotoxicity against L-6-cells. The activity and the cytotoxicity were strongly influenced by the linker and its substitution. The most active compounds showed good activity and promising selectivity.

Original language	English
Article number	5530
Journal	Molecules
Volume	26
Issue number	18
DOIs	https://doi.org/10.3390/molecules26185530
Publication status	Published - Sept 2021

Keywords

8-aminoquinolines
Antimalarial
Plasmodium falciparum
Tetrazole derivatives

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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title = "8-amino-6-methoxyquinoline—tetrazole hybrids: Impact of linkers on antiplasmodial activity",

abstract = "A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against Plasmodium falciparum NF54 as well as their cytotoxicity against L-6-cells. The activity and the cytotoxicity were strongly influenced by the linker and its substitution. The most active compounds showed good activity and promising selectivity.",

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author = "Patrick Hochegger and Johanna Dolensky and Werner Seebacher and Robert Saf and Marcel Kaiser and Pascal M{\"a}ser and Robert Weis",

note = "Funding Information: The authors acknowledge Open Access Funding by the University of Graz. Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

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T2 - Impact of linkers on antiplasmodial activity

AU - Hochegger, Patrick

AU - Dolensky, Johanna

AU - Seebacher, Werner

AU - Saf, Robert

AU - Kaiser, Marcel

AU - Mäser, Pascal

AU - Weis, Robert

PY - 2021/9

Y1 - 2021/9

N2 - A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against Plasmodium falciparum NF54 as well as their cytotoxicity against L-6-cells. The activity and the cytotoxicity were strongly influenced by the linker and its substitution. The most active compounds showed good activity and promising selectivity.

AB - A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against Plasmodium falciparum NF54 as well as their cytotoxicity against L-6-cells. The activity and the cytotoxicity were strongly influenced by the linker and its substitution. The most active compounds showed good activity and promising selectivity.

KW - 8-aminoquinolines

KW - Antimalarial

KW - Plasmodium falciparum

KW - Tetrazole derivatives

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VL - 26

JO - Molecules

JF - Molecules

IS - 18

M1 - 5530

ER -

8-amino-6-methoxyquinoline—tetrazole hybrids: Impact of linkers on antiplasmodial activity

Abstract

Keywords

ASJC Scopus subject areas

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