BRD3444   Click here for help

GtoPdb Ligand ID: 9648

Antimalarial Ligand
Compound class: Synthetic organic
Comment: BRD3444 is the hit compound from a series of bicyclic azetidines with promising antimalarial activity against all lifecycle stages of the Plasmodium parasite [1]. Note that BRD3444 has complex stereoisomers (PubChem same connectivity and via the UniChem InChIKey backbone search in our summary table below).

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 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 65.04
Molecular weight 495.25
XLogP 4.83
No. Lipinski's rules broken 0
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Canonical SMILES OCC1N2CCCCN(CC2C1c1ccc(cc1)C#Cc1ccccc1)C(=O)Nc1ccc(cc1)OC
Isomeric SMILES OC[C@H]1N2CCCCN(C[C@H]2[C@H]1c1ccc(cc1)C#Cc1ccccc1)C(=O)Nc1ccc(cc1)OC
InChI InChI=1S/C31H33N3O3/c1-37-27-17-15-26(16-18-27)32-31(36)33-19-5-6-20-34-28(21-33)30(29(34)22-35)25-13-11-24(12-14-25)10-9-23-7-3-2-4-8-23/h2-4,7-8,11-18,28-30,35H,5-6,19-22H2,1H3,(H,32,36)/t28-,29+,30+/m0/s1
Guide to Malaria Pharmacology Comments
BRD3444 has promising activity against multiple lifecycle stages of the Plasmodium parasite [1]. Note that this paper also discloses BRD1095 and BRD7929, advanced analogues that are more soluble, retain in vitro potency and with the same mechanism of action as BRD3444.

Potential Target/Mechanism Of Action: Correlation of purified cFRS IC50 values against parasite growth inhibition assays for a range of analogues, together with genetic evidence, indicate that PfcFRS is the relevant molecular target of this bicyclic azetidine series [1].