but-2-enedioic acid ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate

• ChemBase编号: 72625
• 分子式: C19H21FN4O6
• 平均质量: 420.3916432
• 单一同位素质量: 420.14451263
• SMILES: c1(ccc(cc1)CNc1nc(c(cc1)NC(=O)OCC)N)F.OC(=O)/C=C/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.CCOC(=O)Nc1ccc(nc1N)NCc1ccc(cc1)F
• InChI: InChI=1S/C15H17FN4O2.C4H4O4/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10;5-3(6)1-2-4(7)8/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20);1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: DPYIXBFZUMCMJM-WLHGVMLRSA-N

名称和登记号

名称

• IUPAC标准名: but-2-enedioic acid ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate; (2E)-but-2-enedioic acid ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate
• IUPAC传统名: butenedioic acid; flupirtine; flupirtine; fumaric acid
• 别名: 2-Amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-carbamic acid ethyl ester maleate salt; Flupirtine maleate salt; Katadolon; Flupirtine maleate

登记号

• CAS号: 75507-68-5
• MDL号: MFCD00941415
• PubChem SID: 162037550; 24278445
• PubChem CID: 6536833

理论计算性质

• Acid pKa: 12.896986
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.9672019
• LogD (pH = 7.4): 2.319763
• Log P: 2.669325
• 摩尔折射率: 85.4865 cm^3
• 极化性: 30.264492 Å^3
• 极化表面积: 89.27 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble >20 mg/mL; H2O: insoluble
• 外观: white solid

安全信息

• 保存条件: -20°C
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 作用靶点: Antimetabolites

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Maleate
• Empirical Formula (Hill Notation): C15H17FN4O2 · C4H4O4

详细说明

Selleck Chemicals - S1334

Research Area

• Description: Cancer

Protocol

• Protocol: Cell Assay ^[4]
• Cell Lines: PC12 cell
• Concentrations: 1 or 5 μg/mL
• Incubation Time: 72 hours
• Methods:

  For measurement of viability and generation of reactive oxygen intermediates, PC12 cells are seeded in 24- or 96-well plates coated with poly-L-lysine at 10^5 cells/mL. Drugs are dissolved in PBS (pH 7.4), or ethanol and filtered sterile. At the end of each experiment cells are trypsinized and pelleted together with cells of the culture supernatant. After staining for 10 min with 0.2% Trypan blue solution live (unstained) and dead (Trypan blue positive) cells are counted in a hemocytometer chamber. In addition, cellular viability is evaluated by the reduction of MTT to formazan. After 2 hours incubation with MTT (0.5 mg/ml) at 37 °C, cells are lysed in DMSO. Extinction at 570 nm is determined on a plate photometer. For staining of surviving adherent cells, plates are incubated for 10 min with 0.5% crystalviolet dissolved in 20% methanol. Plates are rinsed with water and stained cells are lysed in 50% ethanol, 0.1 M sodiumcitrate before determining extinction at 550 nm.

• Protocol: Animal Study ^[7]
• Animal Models: male Wistar rats with cerebral ischemia induced by four-vessel-occlusion
• Formulation: sterile 0.9% sodium chloride solution
• Doses: 5 mg/kg
• Administration: Intraperitoneal injection either 20 min before and 50 min after occlusion or directly and 70 min after occlusion

References

• References: [1] Perovic S, et al. Eur J Pharmacol, 1994, 288(1), 27-33.
• References: [2] Rupalla K, et al. Eur J Pharmacol, 1995, 294(2-3), 469-473
• References: [3] Müller WE, et al. J Neurochem, 1997, 68(6), 2371-2377.
• References: [4] Seyfried J, et al. Eur J Pharmacol, 2000, 400(2-3):155-166.
• References: [5] Dörr J, et al. J Neuroimmunol, 2005, 167(1-2), 204-209.
• References: [6] Kornhuber J, et al. J Neural Transm, 1999, 106(9-10), 857-867.
• References: [7] Block F, et al. Brain Res, 1997, 754(1-2), 279-284.
• References: [8] Bleyer H, et al. Eur J Pharmacol, 1988, 151(2), 259-265.
• References: [9] Nickel B, et al. Arzneimittelforschung, 1990, 40(8), 909-911.

Sigma Aldrich - F8927

Biochem/physiol Actions
Non-opioid analgesic; cytoprotective versus PrP fragment 106-126

参考文献

• Perovic S, et al. Eur J Pharmacol, 1994, 288(1), 27-33.
• Rupalla K, et al. Eur J Pharmacol, 1995, 294(2-3), 469-473
• Müller WE, et al. J Neurochem, 1997, 68(6), 2371-2377.
• Seyfried J, et al. Eur J Pharmacol, 2000, 400(2-3):155-166.
• Dörr J, et al. J Neuroimmunol, 2005, 167(1-2), 204-209.
• Kornhuber J, et al. J Neural Transm, 1999, 106(9-10), 857-867.
• Block F, et al. Brain Res, 1997, 754(1-2), 279-284.
• Bleyer H, et al. Eur J Pharmacol, 1988, 151(2), 259-265.
• Nickel B, et al. Arzneimittelforschung, 1990, 40(8), 909-911.