compound 55 [PMID: 29889526]   Click here for help

GtoPdb Ligand ID: 10016

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Compound 55 is the drug-like lead discovered as a result of a SAR investigation and is a 2,8-Disubstituted-1,5-naphthyridine derivative of MMV024101 [2].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 107.21
Molecular weight 430.07
XLogP 3.15
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES FC(c1nccc(c1)c1ccnc2c1nc(cc2)c1cccc(c1)S(=O)(=O)N)(F)F
Isomeric SMILES FC(c1nccc(c1)c1ccnc2c1nc(cc2)c1cccc(c1)S(=O)(=O)N)(F)F
InChI InChI=1S/C20H13F3N4O2S/c21-20(22,23)18-11-12(6-8-26-18)15-7-9-25-17-5-4-16(27-19(15)17)13-2-1-3-14(10-13)30(24,28)29/h1-11H,(H2,24,28,29)
InChI Key UNHBOZVTSNPRRO-UHFFFAOYSA-N
Bioactivity Comments
Compound 55 shows good in vitro antiplasmodial activity against chloroquine sensitive P. falciparum NF54 and multidrug resistant P. falciparum K1 [2]. It shows no cardiotoxicity risk (hERG IC50 > 10 μM). It was shown to be effective in the in vivo NSG mouse model of P. falciparum infection [1], where it exhibited an IC50 value of 142 nM in mice infected with human specific Pf3D7 [2].
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum phosphatidylinositol 4-kinase PfNF54 - - 7.2 pIC50 - 2
pIC50 7.2 (IC50 6.3x10-8 M) [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Plasmodium falciparum phosphatidylinositol 4-kinase PfK1 - - 7.0 pIC50 - 2
pIC50 7.0 (IC50 1.02x10-7 M) [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)