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Article

New Acyl Derivatives of 3-Aminofurazanes and Their Antiplasmodial Activities

1
Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstraße 1, A-8010 Graz, Austria
2
Institute for Chemistry and Technology of Materials (ICTM), Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria
3
Swiss Tropical and Public Health Institute, Socinstraße 57, CH-4002 Basel, Switzerland
*
Author to whom correspondence should be addressed.
Academic Editor: Marcelo J. Nieto
Pharmaceuticals 2021, 14(5), 412; https://0-doi-org.brum.beds.ac.uk/10.3390/ph14050412
Received: 29 March 2021 / Revised: 21 April 2021 / Accepted: 24 April 2021 / Published: 27 April 2021
(This article belongs to the Special Issue Antiparasitics)
An N-acylated furazan-3-amine of a Medicines for Malaria Venture (MMV) project has shown activity against different strains of Plasmodium falciparum. Seventeen new derivatives were prepared and tested in vitro for their activities against blood stages of two strains of Plasmodium falciparum. Several structure–activity relationships were revealed. The activity strongly depended on the nature of the acyl moiety. Only benzamides showed promising activity. The substitution pattern of their phenyl ring affected the activity and the cytotoxicity of compounds. In addition, physicochemical parameters were calculated (log P, log D, ligand efficiency) or determined experimentally (permeability) via a PAMPA. The N-(4-(3,4-diethoxyphenyl)-1,2,5-oxadiazol-3-yl)-3-(trifluoromethyl)benzamide possessed good physicochemical properties and showed high antiplasmodial activity against a chloroquine-sensitive strain (IC50(NF54) = 0.019 µM) and even higher antiplasmodial activity against a multiresistant strain (IC50(K1) = 0.007 µM). Compared to the MMV compound, the permeability and the activity against the multiresistant strain were improved. View Full-Text
Keywords: antimalarial; furazan derivatives; Plasmodium falciparum; PAMPA antimalarial; furazan derivatives; Plasmodium falciparum; PAMPA
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MDPI and ACS Style

Hermann, T.; Hochegger, P.; Dolensky, J.; Seebacher, W.; Saf, R.; Kaiser, M.; Mäser, P.; Weis, R. New Acyl Derivatives of 3-Aminofurazanes and Their Antiplasmodial Activities. Pharmaceuticals 2021, 14, 412. https://0-doi-org.brum.beds.ac.uk/10.3390/ph14050412

AMA Style

Hermann T, Hochegger P, Dolensky J, Seebacher W, Saf R, Kaiser M, Mäser P, Weis R. New Acyl Derivatives of 3-Aminofurazanes and Their Antiplasmodial Activities. Pharmaceuticals. 2021; 14(5):412. https://0-doi-org.brum.beds.ac.uk/10.3390/ph14050412

Chicago/Turabian Style

Hermann, Theresa, Patrick Hochegger, Johanna Dolensky, Werner Seebacher, Robert Saf, Marcel Kaiser, Pascal Mäser, and Robert Weis. 2021. "New Acyl Derivatives of 3-Aminofurazanes and Their Antiplasmodial Activities" Pharmaceuticals 14, no. 5: 412. https://0-doi-org.brum.beds.ac.uk/10.3390/ph14050412

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