CHF-5074   Click here for help

GtoPdb Ligand ID: 7339

Synonyms: CHF 5074 | CHF5074
PDB Ligand
Compound class: Synthetic organic
Comment: CHF-5074 is a gamma-secretase modulator (GSM). These are small molecules (<600 Da) causing a product shift from Abeta42 toward shorter and less toxic Abeta fragments. Classical non-steroidal anti-inflammatory drugs (NSAIDs) constituted the first class of GSMs. This compound has advanced to phase I trials
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 37.3
Molecular weight 324.01
XLogP 5.38
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)C1(CC1)c1ccc(c(c1)F)c1ccc(c(c1)Cl)Cl
Isomeric SMILES OC(=O)C1(CC1)c1ccc(c(c1)F)c1ccc(c(c1)Cl)Cl
InChI InChI=1S/C16H11Cl2FO2/c17-12-4-1-9(7-13(12)18)11-3-2-10(8-14(11)19)16(5-6-16)15(20)21/h1-4,7-8H,5-6H2,(H,20,21)
1. Ross J, Sharma S, Winston J, Nunez M, Bottini G, Franceschi M, Scarpini E, Frigerio E, Fiorentini F, Fernandez M et al.. (2013)
CHF5074 reduces biomarkers of neuroinflammation in patients with mild cognitive impairment: a 12-week, double-blind, placebo-controlled study.
Curr Alzheimer Res, 10 (7): 742-53. [PMID:23968157]
2. Xin Z, Peng H, Zhang A, Talreja T, Kumaravel G, Xu L, Rohde E, Jung MY, Shackett MN, Kocisko D et al.. (2011)
Discovery of 4-aminomethylphenylacetic acids as γ-secretase modulators via a scaffold design approach.
Bioorg Med Chem Lett, 21 (24): 7277-80. [PMID:22061640]