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@article{2243545,
author = {Kos, Jiří and Degotte, Gilles and Pindjakova, Dominika and Strhársky, Tomáš and Jankech, Timotej and Goněc, Tomáš and Francotte, Pierre and Frederich, Michel and Jampilek, Josef},
article_location = {Basel},
article_number = {22},
doi = {http://dx.doi.org/10.3390/molecules27227799},
keywords = {cinnamanilides; antiplasmodial activity; Plasmodium; structure-activity relationships},
language = {eng},
issn = {1420-3049},
journal = {Molecules},
title = {Insights into Antimalarial Activity of N-Phenyl-Substituted Cinnamanilides},
url = {https://www.mdpi.com/1420-3049/27/22/7799},
volume = {27},
year = {2022}
}
TY - JOUR
ID - 2243545
AU - Kos, Jiří - Degotte, Gilles - Pindjakova, Dominika - Strhársky, Tomáš - Jankech, Timotej - Goněc, Tomáš - Francotte, Pierre - Frederich, Michel - Jampilek, Josef
PY - 2022
TI - Insights into Antimalarial Activity of N-Phenyl-Substituted Cinnamanilides
JF - Molecules
VL - 27
IS - 22
SP - 1-10
EP - 1-10
PB - MDPI
SN - 14203049
KW - cinnamanilides
KW - antiplasmodial activity
KW - Plasmodium
KW - structure-activity relationships
UR - https://www.mdpi.com/1420-3049/27/22/7799
N2 - Due to the urgent need of innovation in the antimalarial therapeutic arsenal, a series of thirty-seven ring-substituted N-arylcinnamanilides prepared by microwave-assisted synthesis were subjected to primary screening against the chloroquine-sensitive strain of P. falciparum 3D7/MRA-102. The lipophilicity of all compounds was experimentally determined as the logarithm of the capacity factor k, and these data were subsequently used in the discussion of structure-activity relationships. Among the screened compounds, fourteen derivatives exhibited IC50 from 0.58 to 31 µM, whereas (2E)-N-(4-bromo-2-chlorophenyl)-3-phenylprop-2-enamide (24) was the most effective agent (IC50 = 0.58 µM). In addition, (2E)-N-[2,6-dibromo-4-(trifluoromethyl)- phenyl]-3-phenylprop-2-enamide (36), (2E)-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-phenylprop- 2-enamide (18), (2E)-N-(2-bromo-5-fluorophenyl)-3-phenylprop-2-enamide (23), and (2E)-3-phenyl-N-(3,4,5-trichlorophenyl)prop-2-enamide (33) demonstrated efficacy in the IC50 range from 2.0 to 4.3 µM, comparable to the clinically used standard chloroquine. The results of a cell viability screening performed using THP1-Blue™ NF-κB cells showed that none of these highly active compounds displayed any significant cytotoxic effect up to 20 μM, which makes them promising Plasmodium selective substances for further investigations.
ER -
KOS, Jiří, Gilles DEGOTTE, Dominika PINDJAKOVA, Tomáš STRHÁRSKY, Timotej JANKECH, Tomáš GONĚC, Pierre FRANCOTTE, Michel FREDERICH and Josef JAMPILEK. Insights into Antimalarial Activity of N-Phenyl-Substituted Cinnamanilides. \textit{Molecules}. Basel: MDPI, 2022, vol.~27, No~22, p.~1-10. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules27227799.
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