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Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives
J. Guillon, A. Cohen, C. Boudot, A. Valle, V. Milano, RN. Das, A. Guédin, S. Moreau, L. Ronga, S. Savrimoutou, M. Demourgues, E. Reviriego, S. Rubio, S. Ferriez, P. Agnamey, C. Pauc, S. Moukha, P. Dozolme, SD. Nascimento, P. Laumaillé, A....
Language English Country Great Britain
Document type Journal Article
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- MeSH
- Antiprotozoal Agents chemical synthesis chemistry pharmacology MeSH
- Hep G2 Cells MeSH
- Quinolines chemical synthesis chemistry pharmacology MeSH
- Leishmania donovani drug effects MeSH
- Humans MeSH
- Plasmodium falciparum drug effects MeSH
- Drug Design * MeSH
- Trypanosoma brucei brucei drug effects MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
A series of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline, and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives was designed, synthesised, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani, and Trypanosoma brucei brucei). Biological results showed antiprotozoal activity with IC50 values in the µM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The quinoline 1c was identified as the most potent antimalarial candidate with a ratio of cytotoxic to antiparasitic activities of 97 against the P. falciparum CQ-sensitive strain 3D7. The quinazoline 3h was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 43 on T. brucei brucei strain. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma are possible targets of this kind of nitrogen heterocyclic compounds, we have also investigated stabilisation of the Plasmodium and Trypanosoma telomeric G-quadruplexes by our best compounds through FRET melting assays.
IRD AP HM SSA VITROME Aix Marseille University Marseille France
PREM UMR5254 UPPA CNRS Technopole Hélioparc Université de Pau Pau France
UFR de Pharmacie AGIR Université de Picardie Jules Verne Amiens France
References provided by Crossref.org
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