NB-360   Click here for help

GtoPdb Ligand ID: 9822

Synonyms: NB360
PDB Ligand
Compound class: Synthetic organic
Comment: Due to good brain penetration, oral doses of Novartis NB-360 completely block amyloid-β deposition in an APP transgenic mouse model [3]. Data across species suggest similar treatment effects can possibly be achieved in humans. The reduced neuroinflammation upon amyloid reduction by NB-360 treatment supports the notion that targeting amyloid-β pathology can have beneficial downstream effects on the progression of Alzheimer's disease. Note this inhibitor is equipotent against BACE2 in vitro. NB-360 did not progress to clinical development, but is suitable as an effective pharmacological tool to investigate the effects of BACE-1 inhibition in Alzherimer's disease models [2]. There is a recent paper describing impairment of synaptic plasticity in mice via Seizure Protein 6 [4]. One of the Novartis patents has a SAR set of 184 IC50 values [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 113.39
Molecular weight 449.15
XLogP 2.63
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#Cc1cnc(c(c1)C)C(=O)Nc1ccc(c(c1)C1(C)COC(C(=N1)N)(C)C(F)(F)F)F
Isomeric SMILES N#Cc1cnc(c(c1)C)C(=O)Nc1ccc(c(c1)[C@]1(C)CO[C@@](C(=N1)N)(C)C(F)(F)F)F
InChI InChI=1S/C21H19F4N5O2/c1-11-6-12(8-26)9-28-16(11)17(31)29-13-4-5-15(22)14(7-13)19(2)10-32-20(3,18(27)30-19)21(23,24)25/h4-7,9H,10H2,1-3H3,(H2,27,30)(H,29,31)/t19-,20+/m0/s1
InChI Key BQFHTVUWPJXLOW-VQTJNVASSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[3-[(3R,6R)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2H-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyano-3-methylpyridine-2-carboxamide
Synonyms Click here for help
NB360
Database Links Click here for help
ChEMBL Ligand CHEMBL3261067
GtoPdb PubChem SID 354702293
PubChem CID 66665322
RCSB PDB Ligand SLK
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