5-amino-7-methoxyindole-2-carboxylic acid methyl ester | 860022-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-amino-7-methoxyindole-2-carboxylic acid methyl ester
• 英文别名: methyl 5-amino-7-methoxy-1H-indole-2-carboxylate
• CAS: 860022-15-7
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: FQBIDFSBHMABCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-7-methoxyindole-2-carboxylic acid methyl ester 在 calcium sulfate 、 溶剂黄146 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 0.5h， 生成 4-Methoxy-7-methyl-9-oxo-6,9-dihydro-3H-pyrrolo[3,2-f]quinoline-2-carboxylic acid methyl ester
  参考文献：
  名称：

  New water soluble pyrroloquinoline derivatives as new potential anticancer agents

  摘要：

  A new class of water soluble 3H-pyrrolo[3,2-f]quinoline derivatives has been synthesized and investigated as potential anticancer drugs. Water solubility profiles have been used to select the most promising derivatives. The novel compound 10, having two (2-diethylamino-ethyl) side chains linked through positions 3N and 90, presents a suitable water solubility profile, and it was shown to exhibit cell growth inhibitory properties when tested against the in-house panel of cell lines, in particular those obtained from melanoma. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.080
• 作为产物：
  描述：

  7-methoxy-5-nitro-1H-indole-2-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 以96%的产率得到5-amino-7-methoxyindole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  New water soluble pyrroloquinoline derivatives as new potential anticancer agents

  摘要：

  A new class of water soluble 3H-pyrrolo[3,2-f]quinoline derivatives has been synthesized and investigated as potential anticancer drugs. Water solubility profiles have been used to select the most promising derivatives. The novel compound 10, having two (2-diethylamino-ethyl) side chains linked through positions 3N and 90, presents a suitable water solubility profile, and it was shown to exhibit cell growth inhibitory properties when tested against the in-house panel of cell lines, in particular those obtained from melanoma. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.080

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.
• New water soluble pyrroloquinoline derivatives as new potential anticancer agents
  作者：Maria Grazia Ferlin、Christine Marzano、Lisa Dalla Via、Adriana Chilin、Giuseppe Zagotto、Adriano Guiotto、Stefano Moro

  DOI：10.1016/j.bmc.2005.04.080

  日期：2005.8

  A new class of water soluble 3H-pyrrolo[3,2-f]quinoline derivatives has been synthesized and investigated as potential anticancer drugs. Water solubility profiles have been used to select the most promising derivatives. The novel compound 10, having two (2-diethylamino-ethyl) side chains linked through positions 3N and 90, presents a suitable water solubility profile, and it was shown to exhibit cell growth inhibitory properties when tested against the in-house panel of cell lines, in particular those obtained from melanoma. (c) 2005 Elsevier Ltd. All rights reserved.