N'-[(5-methylfuran-2-yl)methylidene]-2-phenoxybenzohydrazide

• ChemBase ID: 154525
• Molecular Formular: C19H16N2O3
• Molecular Mass: 320.34194
• Monoisotopic Mass: 320.11609238
• SMILES: Cc1ccc(o1)/C=N\NC(=O)c1ccccc1Oc1ccccc1
• Canonical SMILES: Cc1ccc(o1)/C=N\NC(=O)c1ccccc1Oc1ccccc1
• InChI: InChI=1S/C19H16N2O3/c1-14-11-12-16(23-14)13-20-21-19(22)17-9-5-6-10-18(17)24-15-7-3-2-4-8-15/h2-13H,1H3,(H,21,22)
• InChIKey: JJEDWBQZCRESJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N'-[(5-methylfuran-2-yl)methylidene]-2-phenoxybenzohydrazide
• IUPAC Traditional name: N'-[(5-methylfuran-2-yl)methylidene]-2-phenoxybenzohydrazide
• Synonyms: Benzoic acid, 2-phenoxy-, 2-[(5-methyl-2-furanyl)methylene]hydrazide; PNU-74654

Database IDs

• CAS Number: 113906-27-7
• MDL Number: MFCD12912438
• PubChem SID: 162248664
• PubChem CID: 68672283

CALCULATED PROPERTIES

• Acid pKa: 9.797059
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.72321
• LogD (pH = 7.4): 3.7216911
• Log P: 3.72323
• Molar Refractivity: 92.0169 cm^3
• Polarizability: 34.27292 Å^3
• Polar Surface Area: 63.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H16N2O3

DETAILS

Sigma Aldrich - P0052

Biochem/physiol Actions
PNU-74654 inhibits the Wnt-β catenin pathway by blocking the interaction between β-catenin and TCF (T cell factor). PNU-74654 is also an anti-tumor agent. Aberrant activation of the Wnt/β-catenin pathway (canonical pathway) is implicated in driving development/progression of different tumors, such as colon cancer, through interaction between β-catenin and T cell factor (TCF), which regulates the expression of target genes in cell proliferation and differentiation. Inhibition of this pathway activity in cancer cell lines efficiently blocks their growth. PNU-74654 inhibits this pathway by blocking the interaction between β-catenin and TCF.