3-[(4-hydroxyphenyl)methylidene]-5,6-dimethoxy-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 154478
• Molecular Formular: C17H15NO4
• Molecular Mass: 297.3053
• Monoisotopic Mass: 297.10010797
• SMILES: COc1cc2c(cc1OC)NC(=O)/C/2=C\c1ccc(cc1)O
• Canonical SMILES: COc1cc2c(cc1OC)NC(=O)/C/2=C\c1ccc(cc1)O
• InChI: InChI=1S/C17H15NO4/c1-21-15-8-12-13(7-10-3-5-11(19)6-4-10)17(20)18-14(12)9-16(15)22-2/h3-9,19H,1-2H3,(H,18,20)
• InChIKey: JGSMCYNBVCGIHC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4-hydroxyphenyl)methylidene]-5,6-dimethoxy-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 3-[(4-hydroxyphenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one
• Synonyms: 1,3-dihydro-5,6-dimethoxy-3-[(4-hydroxyphenyl)methylene]-H-indol-2-one; RPI-1

Database IDs

• CAS Number: 269730-03-2
• MDL Number: MFCD03852474
• PubChem SID: 162248617
• PubChem CID: 1749978

CALCULATED PROPERTIES

• Acid pKa: 9.352423
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.6462617
• LogD (pH = 7.4): 2.6415336
• Log P: 2.6463223
• Molar Refractivity: 84.6386 cm^3
• Polarizability: 31.451914 Å^3
• Polar Surface Area: 67.79 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: orange powder

Safety Information

• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H15NO4

DETAILS

Sigma Aldrich - R8907

Biochem/physiol Actions
RPI-1 is a competitive, potent ATP-dependent Ret kinase inhibitor. Recently it was discover that the compound also inhibits c-Met. Increased tumorigenicity, motility, and invasiveness have been described as biological consequences of HGF/Met deregulation in tumor cells, thus not surprisingly RPI-1 treatment of H460 cells resulted in a strong reduction of both colony number and size (IC50 = 24.5 + 0.5 microM). Compound is also active at mouse NSCLC H460 xenograft tumor and metastasis model. Mechanistically RPI-1 inhibits Met phosphorylation at Tyr1234/Tyr1235, known to activate the intrinsic kinase activity. It appears that " Ret/ptc1 cross talks with Met at transcriptional and signaling levels and promotes ?-catenin transcriptional activity to drive thyrocyte neoplastic transformation". It appears that we do not have anything specific in Ret area. Handbook lists RPI-1 as Ret inhibitor.