N-{4-[3-(3-oxo-1H-pyrrolo[3,4-b]quinolin-2(3H)-yl)propyl] phenyl}acetic acid | 1370636-15-9

• 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: N-{4-[3-(3-oxo-1H-pyrrolo[3,4-b]quinolin-2(3H)-yl)propyl] phenyl}acetic acid
• CAS: 1370636-15-9
• 化学式: C₂₂H₂₀N₂O₃
• 分子量: 360.412
• InChiKey: OLPSBLAGLRNXSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70.5
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-硝基苯基)哌嗪 、 N-{4-[3-(3-oxo-1H-pyrrolo[3,4-b]quinolin-2(3H)-yl)propyl] phenyl}acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以69%的产率得到2-[3-[4-[2-[4-(4-nitrophenyl)piperazin-1-yl]-2-oxoethyl]phenyl]propyl]-1H-pyrrolo[3,4-b]quinolin-3-one
  参考文献：
  名称：

  Synthesis of novel building blocks of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one and evaluation of their antitumor activity

  摘要：

  A series of new building blocks consisting of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one with potential as selective antitumor agents is described. Compounds were synthesized by using Heck reaction of N-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one with p-bromophenyl acetic acid followed by formation of amide (1a-h, 2a-d) by reaction with several secondary amines in good yields. The cytotoxicity of these compounds was evaluated against human cancer cell lines in vitro (SK-N-NH, A549). Studies suggest that most of these compounds were effective in inhibiting neuroblastoma cell growth, compound 1d was the most potent one (% IC50 = 8.62 mu M).

  DOI：

  10.1007/s00044-012-0018-x
• 作为产物：
  描述：

  1-(二甲氧基甲基)-2-氨基苯 在 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 caesium carbonate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成 N-{4-[3-(3-oxo-1H-pyrrolo[3,4-b]quinolin-2(3H)-yl)propyl] phenyl}acetic acid
  参考文献：
  名称：

  Synthesis of novel building blocks of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one and evaluation of their antitumor activity

  摘要：

  A series of new building blocks consisting of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one with potential as selective antitumor agents is described. Compounds were synthesized by using Heck reaction of N-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one with p-bromophenyl acetic acid followed by formation of amide (1a-h, 2a-d) by reaction with several secondary amines in good yields. The cytotoxicity of these compounds was evaluated against human cancer cell lines in vitro (SK-N-NH, A549). Studies suggest that most of these compounds were effective in inhibiting neuroblastoma cell growth, compound 1d was the most potent one (% IC50 = 8.62 mu M).

  DOI：

  10.1007/s00044-012-0018-x