3-phenyl-3-(1-methylindol-4-ylamino)acrylic acid ethyl ester | 852715-69-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-phenyl-3-(1-methylindol-4-ylamino)acrylic acid ethyl ester
• 英文别名: ethyl 3-[(1-methylindol-4-yl)amino]-3-phenylprop-2-enoate
• CAS: 852715-69-6
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: CPXCRCVMAYWTJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  43.26
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-3-(1-methylindol-4-ylamino)acrylic acid ethyl ester 以 二苯醚 为溶剂， 反应 0.5h， 以37%的产率得到7-methyl-2-phenyl-1H-pyrrolo[2,3-h]quinolin-4-one
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antitumor Activity of 2-Phenylpyrroloquinolin-4-ones

  摘要：

  In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26, when tested against a panel of fourteen human tumor cell lines, showed poor in vitro cytotoxic activity, whereas 20, 21 and 24 showed significant activity (IC50 0.7 to 50 mu M). Steroid hormone-sensitive ovary, liver, breast and adrenal gland adenocarcinoma cell lines displayed the highest sensitivity (IC50 0.7 to 8,mu M). Compound 24 blocked cells in the G(2)/M phase of the cell cycle and induced a significant increase in apoptotis. Compounds 20, 21 and 24 proved to alter microtubule assembly and stability, displaying a cytoplasmic microtubule network similar to that caused by Vincristine. In vivo, administration of compound 24 to Balb/c mice inhibited the growth of a syngenic hepatocellular carcinoma.

  DOI：

  10.1021/jm049387x
• 作为产物：
  描述：

  2-甲基-3-硝基苯胺 在 盐酸 、 calcium sulfate 、 氢氧化钾 、 titanium(III) chloride 、 potassium ethoxide 、 对甲苯磺酸 、 溶剂黄146 、 草酸二乙酯 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 52.0h， 生成 3-phenyl-3-(1-methylindol-4-ylamino)acrylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Antitumor Activity of 2-Phenylpyrroloquinolin-4-ones

  摘要：

  In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26, when tested against a panel of fourteen human tumor cell lines, showed poor in vitro cytotoxic activity, whereas 20, 21 and 24 showed significant activity (IC50 0.7 to 50 mu M). Steroid hormone-sensitive ovary, liver, breast and adrenal gland adenocarcinoma cell lines displayed the highest sensitivity (IC50 0.7 to 8,mu M). Compound 24 blocked cells in the G(2)/M phase of the cell cycle and induced a significant increase in apoptotis. Compounds 20, 21 and 24 proved to alter microtubule assembly and stability, displaying a cytoplasmic microtubule network similar to that caused by Vincristine. In vivo, administration of compound 24 to Balb/c mice inhibited the growth of a syngenic hepatocellular carcinoma.

  DOI：

  10.1021/jm049387x