Ethyl 6-bromo-4-[4-fluoro-3-(trifluoromethyl)anilino]quinoline-3-carboxylate | 1266689-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Ethyl 6-bromo-4-[4-fluoro-3-(trifluoromethyl)anilino]quinoline-3-carboxylate
• CAS: 1266689-65-9
• 化学式: C₁₉H₁₃BrF₄N₂O₂
• 分子量: 457.222
• InChiKey: YTEZTTLTGQHHDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 6-bromo-4-[4-fluoro-3-(trifluoromethyl)anilino]quinoline-3-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 [6-Bromo-4-[4-fluoro-3-(trifluoromethyl)anilino]quinolin-3-yl]methanol
  参考文献：
  名称：

  Discovery of 9-(6-Aminopyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one (Torin2) as a Potent, Selective, and Orally Available Mammalian Target of Rapamycin (mTOR) Inhibitor for Treatment of Cancer

  摘要：

  The mTOR mediated PI3K/AKT/mTOR signal transduction pathway has been demonstrated to play a key role in a broad spectrum of cancers. Starting from the mTOR selective inhibitor 1 (Torin1), a focused medicinal chemistry effort led to the discovery of an improved mTOR inhibitor 3 (Torin2), which possesses an EC(50) of 0.25 nM for inhibiting cellular mTOR activity. Compound 3 exhibited 800-fold selectivity over PI3K (EC(50): 200 nM) and over 100-fold binding selectivity relative to 440 other protein kinases. Compound 3 has significantly improved bioavailability (54%), metabolic stability, and plasma exposure relative to compound 1.

  DOI：

  10.1021/jm101520v
• 作为产物：
  描述：

  4-氟-3-三氟甲基苯胺 、 6-溴-4-氯-3-喹啉羧酸乙酯 以 1,4-二氧六环 为溶剂， 生成 Ethyl 6-bromo-4-[4-fluoro-3-(trifluoromethyl)anilino]quinoline-3-carboxylate
  参考文献：
  名称：

  Discovery of 9-(6-Aminopyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one (Torin2) as a Potent, Selective, and Orally Available Mammalian Target of Rapamycin (mTOR) Inhibitor for Treatment of Cancer

  摘要：

  The mTOR mediated PI3K/AKT/mTOR signal transduction pathway has been demonstrated to play a key role in a broad spectrum of cancers. Starting from the mTOR selective inhibitor 1 (Torin1), a focused medicinal chemistry effort led to the discovery of an improved mTOR inhibitor 3 (Torin2), which possesses an EC(50) of 0.25 nM for inhibiting cellular mTOR activity. Compound 3 exhibited 800-fold selectivity over PI3K (EC(50): 200 nM) and over 100-fold binding selectivity relative to 440 other protein kinases. Compound 3 has significantly improved bioavailability (54%), metabolic stability, and plasma exposure relative to compound 1.

  DOI：

  10.1021/jm101520v