GSK369796   Click here for help

GtoPdb Ligand ID: 10411

Synonyms: N-tert-Butyl isoquine
Antimalarial Ligand
Compound class: Synthetic organic
Comment: GSK369796 is a 4-aminoquinoline antimalarial compound that was synthesised using amodiaquine as the template molecule [3].

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 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 57.18
Molecular weight 355.15
XLogP 4.79
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc2c(c1)nccc2Nc1ccc(c(c1)O)CNC(C)(C)C
Isomeric SMILES Clc1ccc2c(c1)nccc2Nc1ccc(c(c1)O)CNC(C)(C)C
InChI InChI=1S/C20H22ClN3O/c1-20(2,3)23-12-13-4-6-15(11-19(13)25)24-17-8-9-22-18-10-14(21)5-7-16(17)18/h4-11,23,25H,12H2,1-3H3,(H,22,24)
Guide to Malaria Pharmacology Comments
GSK369796 was developed by academics at Liverpool as part of a public-private partnership managed by the Medicines for Malaria Venture (MMV) [3]. This research collaboration, utilised the 4-aminoquinoline scaffold of amodiaquine to design and synthesise derivatives active against both chloroquine-susceptible and chloroquine-resistant P. falciparum strains.

Potential Target/Mechanism Of Action: As the precise MOA of GSK369796 is not yet known, we do not have a molecular target for this compound. It is thought that GSK369796 has a similar MOA to chloroquine, killing the malaria parasite by causing a build up of toxic heme by inhibiting the enzyme that normally converts it to non-toxic haemozoin [1].