ethyl 3-(m-nitro-phenyl)-3-(indol-5-ylamino)-acrylate

• 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: ethyl 3-(m-nitro-phenyl)-3-(indol-5-ylamino)-acrylate
• 英文别名: ethyl (E)-3-(1H-indol-5-ylamino)-3-(3-nitrophenyl)prop-2-enoate
• 化学式: C₁₉H₁₇N₃O₄
• 分子量: 351.362
• InChiKey: RODUUPPCAUJBNM-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(m-nitro-phenyl)-3-(indol-5-ylamino)-acrylate 以 二苯醚 为溶剂， 反应 0.5h， 以75%的产率得到7-(3-Nitro-phenyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-9-one
  参考文献：
  名称：

  Synthesis and Biological Activity of 7-Phenyl-6,9-dihydro-3H-pyrrolo[3,2-f]quinolin-9-ones:  A New Class of Antimitotic Agents Devoid of Aromatase Activity

  摘要：

  The newly synthesized 7-phenyl-3H-pyrrolo[3,2-f]quinolinones 16-26 and previously 27 and 28 were assayed for their in vitro antiproliferative activity on tumor cell lines, and the lead compound 16 in vivo on a singenic hepatocellular carcinoma in Balb/c mice. Results from FACS, immunofluorescence microscopy analysis, tubulin polymerization assay, and tritiated water release assay for the CYP19 activity confirmed the new compounds as potential anticancer agents acting by tubulin depolymerization, but devoid of aromatase activity unlike their geometric [2,3-h] isomers.

  DOI：

  10.1021/jm0510676
• 作为产物：
  描述：

  5-氨基吲哚 、 3-硝基苯甲酰乙酸乙酯 在 calcium sulfate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以48%的产率得到ethyl 3-(m-nitro-phenyl)-3-(indol-5-ylamino)-acrylate
  参考文献：
  名称：

  Synthesis and Biological Activity of 7-Phenyl-6,9-dihydro-3H-pyrrolo[3,2-f]quinolin-9-ones:  A New Class of Antimitotic Agents Devoid of Aromatase Activity

  摘要：

  The newly synthesized 7-phenyl-3H-pyrrolo[3,2-f]quinolinones 16-26 and previously 27 and 28 were assayed for their in vitro antiproliferative activity on tumor cell lines, and the lead compound 16 in vivo on a singenic hepatocellular carcinoma in Balb/c mice. Results from FACS, immunofluorescence microscopy analysis, tubulin polymerization assay, and tritiated water release assay for the CYP19 activity confirmed the new compounds as potential anticancer agents acting by tubulin depolymerization, but devoid of aromatase activity unlike their geometric [2,3-h] isomers.

  DOI：

  10.1021/jm0510676

文献信息

• Synthesis and Biological Activity of 7-Phenyl-6,9-dihydro-3<i>H</i>-pyrrolo[3,2-<i>f</i>]quinolin-9-ones:  A New Class of Antimitotic Agents Devoid of Aromatase Activity
  作者：Venusia Gasparotto、Ignazio Castagliuolo、Gianfranco Chiarelotto、Vincenzo Pezzi、Daniela Montanaro、Paola Brun、Giorgio Palù、Giampietro Viola、Maria Grazia Ferlin

  DOI：10.1021/jm0510676

  日期：2006.3.1

  The newly synthesized 7-phenyl-3H-pyrrolo[3,2-f]quinolinones 16-26 and previously 27 and 28 were assayed for their in vitro antiproliferative activity on tumor cell lines, and the lead compound 16 in vivo on a singenic hepatocellular carcinoma in Balb/c mice. Results from FACS, immunofluorescence microscopy analysis, tubulin polymerization assay, and tritiated water release assay for the CYP19 activity confirmed the new compounds as potential anticancer agents acting by tubulin depolymerization, but devoid of aromatase activity unlike their geometric [2,3-h] isomers.