7-methoxy-5-nitro-1H-indole-2-carboxylic acid methyl ester | 539856-41-2

• 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: 7-methoxy-5-nitro-1H-indole-2-carboxylic acid methyl ester
• 英文别名: methyl 7-methoxy-5-nitro-1H-indole-2-carboxylate；1H-Indole-2-carboxylic acid, 7-methoxy-5-nitro-, methyl ester
• CAS: 539856-41-2
• 化学式: C₁₁H₁₀N₂O₅
• 分子量: 250.211
• InChiKey: WJOFPZYCWJKOPV-UHFFFAOYSA-N

物化性质

• 熔点：
  205-210 °C(Solv: ethanol (64-17-5))
• 沸点：
  467.1±40.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 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：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-methoxy-5-nitro-1H-indole-2-carboxylic acid methyl ester 在 palladium on activated charcoal calcium sulfate 、 氢气 、 溶剂黄146 作用下， 以 二苯醚 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 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：

  (E)-2-[(2-methoxy-4-nitrophenyl)hydrazono]propionic acid methyl ester 在 PPA 作用下， 以 xylene 为溶剂， 反应 18.0h， 以64%的产率得到7-methoxy-5-nitro-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  一种简洁高效的seco-Duocarmycin SA的合成

  摘要：

  已经实现了一种高效细胞抑制剂和天然产物 duocarmycin SA (1) 的直接前体 seco-duocarmycin SA (3) 的简短有效合成。从市售的 2-甲氧基-4-硝基苯胺 (4) 开始，合成方案包含 Fischer 吲哚合成以引入杂环支架和自由基 5-exo-trig 环化以提供（氯甲基）二氢吲哚环系统作为关键反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200390094

文献信息

• 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.
• A Concise and Efficient Synthesis ofseco-Duocarmycin SA
  作者：Lutz F. Tietze、Frank Haunert、Tim Feuerstein、Tobias Herzig

  DOI：10.1002/ejoc.200390094

  日期：2003.2

  A short and efficient synthesis of seco-duocarmycin SA (3), a highly potent cytostatic agent and direct precursor of the natural product duocarmycin SA (1), has been achieved. Starting from commercially available 2-methoxy-4-nitroaniline (4) the synthetic protocol contains a Fischer indole synthesis to introduce the heterocyclic scaffold and a radical 5-exo-trig cyclization to furnish the (chloromethyl)indoline

  已经实现了一种高效细胞抑制剂和天然产物 duocarmycin SA (1) 的直接前体 seco-duocarmycin SA (3) 的简短有效合成。从市售的 2-甲氧基-4-硝基苯胺 (4) 开始，合成方案包含 Fischer 吲哚合成以引入杂环支架和自由基 5-exo-trig 环化以提供（氯甲基）二氢吲哚环系统作为关键反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)