1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid

• ChemBase编号: 70625
• 分子式: C15H10Cl2N2O2
• 平均质量: 321.1581
• 单一同位素质量: 320.01193293
• SMILES: n1(nc(c2ccccc12)C(=O)O)Cc1c(cc(cc1)Cl)Cl
• Canonical SMILES: Clc1ccc(c(c1)Cl)Cn1nc(c2c1cccc2)C(=O)O
• InChI: InChI=1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)
• InChIKey: WDRYRZXSPDWGEB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid
• IUPAC传统名: DICA
• 别名: 1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid; Lonidamine; 1-(2,4-Dichlorobenzyl)-1H-indazole-3-carboxylic acid; Diclondazolic acid; Lonidamine

登记号

• CAS号: 50264-69-2
• EC号: 256-510-0
• MDL号: MFCD00866285
• PubChem SID: 24278515; 162036340
• PubChem CID: 39562

理论计算性质

• Acid pKa: 3.1167057
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.040736
• LogD (pH = 7.4): 0.9369768
• Log P: 4.3959794
• 摩尔折射率: 92.3955 cm^3
• 极化性: 32.088455 Å^3
• 极化表面积: 55.12 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: -20°C
• 保存注意事项: IRRITANT
• RTECS编号: NK7886000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 60-22-40
• 安全公开号: 53-22-36/37/39-45
• TSCA收录: false
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H351-H360
• GHS警示性声明: P201-P281-P308 + P313
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

产品相关信息

• 纯度: 95+%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C15H10Cl2N2O2

详细说明

Selleck Chemicals - S2610

Research Area: Cancer
Biological Activity:
Lonidamine is an orally administered small molecule hexokinase inactivator with an IC50 of 0.85 mM. Lonidamine inhibits glycolysis by the inactivation of hexokinase. Interestingly, Lonidamine seems to enhance aerobic glycolysis in normal cells, but suppress glycolysis in cancer cells. This is most likely through the inhibition of the mitochondrially bound hexokinase. Lonidamine inhibits both respiration and glycolysis leading to a decrease in cellular ATP. In addition, lonidamine may increase programmed cell death. This stems from the observation that mitochondria and mitochondria-bound hexokinase are crucial for induction of apoptosis. In vitro models with lonidamine exhibit the hallmarks of apoptosis, including mitochondrial membrane depolarization, release of cytochrome C, phosphatidylserine externalization, and DNA fragmentation. Lonidamine also blocks CFTR Cl- channels in vitro. [1][2][3][4]References on Lonidamine[1] http://en.wikipedia.org/wiki/Lonidamine, , [2] Mol Biochem Parasitol., 2008 Apr, 158(2):202-7[3] Cancer Chemother Pharmacol. , 1989, 25(1):32-6[4] Rev Urol. , 2005, 7 Suppl 7:S21-6

Sigma Aldrich - L4900

Biochem/physiol Actions
Inhibits the energy metabolism of neoplastic cells by interfering with hexokinase and disrupting uncoupler-stimulated mitochondrial electron transport;1 damages cell and mitochondrial membranes.