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

• ChemBase编号: 154478
• 分子式: C17H15NO4
• 平均质量: 297.3053
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-[(4-hydroxyphenyl)methylidene]-5,6-dimethoxy-2,3-dihydro-1H-indol-2-one
• IUPAC传统名: 3-[(4-hydroxyphenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one
• 别名: 1,3-dihydro-5,6-dimethoxy-3-[(4-hydroxyphenyl)methylene]-H-indol-2-one; RPI-1

登记号

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

理论计算性质

• Acid pKa: 9.352423
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 2.6462617
• LogD (pH = 7.4): 2.6415336
• Log P: 2.6463223
• 摩尔折射率: 84.6386 cm^3
• 极化性: 31.451914 Å^3
• 极化表面积: 67.79 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL
• 外观: orange powder

安全信息

• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N)
• 德国WGK号: 3
• 危险公开号: 50/53
• 安全公开号: 60-61
• GHS危险品标识: GHS09
• GHS警示词: Warning
• GHS危险声明: H400
• GHS警示性声明: P273
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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.