5-chloro-1-(2-(3-nitrophenyl)-2-oxoethyl)quinolin-1-ium bromide | 1174987-68-8

• 英文名称: 5-chloro-1-(2-(3-nitrophenyl)-2-oxoethyl)quinolin-1-ium bromide
• CAS: 1174987-68-8
• 化学式: Br*C₁₇H₁₂ClN₂O₃
• 分子量: 407.651
• InChiKey: XCPKIGHKJIQUEI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-氯喹啉 、 2-溴-3'-硝基苯乙酮 以 乙腈 为溶剂， 生成 5-chloro-1-(2-(3-nitrophenyl)-2-oxoethyl)quinolin-1-ium bromide
  参考文献：
  名称：

  Discovery of 1-benzoyl-3-cyanopyrrolo[1,2-a]quinolines as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2: Structure–activity relationships of the 4-, 5-, 6-, 7- and 8-positions

  摘要：

  As a continuation of our efforts to discover and develop the apoptosis inducing 1-benzoyl-3-cyanopyrrolo[1,2-a] quinolines as potential anticancer agents, we explored substitutions at the 4-, 5-, 6-, 7- and 8-positions of pyrrolo[1,2-a] quinoline. SAR studies showed that substitution at the 6- position by a small group such as Cl resulted in potent compounds. Substitutions at the 5- and 8-positions were tolerated while substitutions at the 4- and 7- position led to inactive compounds. Several compounds, including 2c, 3a, 3b and 3f, were found to be highly active against human breast cancer cells T47D with EC50 values of 0.053-0.080 mu M, but much less active against human colon cancer cells HCT116 and hepatocellular carcinoma cancer cells SNU398 in the caspase activation assay. Compound 3f also was found to be highly active with a GI(50) value of 0.018 mu M against T47D cells in a growth inhibition assay. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.012