2-chloro-5-methoxy-1,6-dimethyl-1H-indole-3-carbaldehyde | 945482-73-5

• 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: 2-chloro-5-methoxy-1,6-dimethyl-1H-indole-3-carbaldehyde
• 英文别名: 2-Chloro-5-methoxy-1,6-dimethylindole-3-carbaldehyde
• CAS: 945482-73-5
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: QWIVVWZNVOOWGI-UHFFFAOYSA-N

物化性质

• 熔点：
  180-183 °C(Solv: ligroine (8032-32-4))
• 沸点：
  390.6±37.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-5-methoxy-1,6-dimethyl-1H-indole-3-carbaldehyde 、 2-吲哚酮 在 sodium carbonate 、 聚甘氨酸 作用下， 以 水 为溶剂， 反应 24.0h， 以22%的产率得到(3E)-3-[(2-chloro-5-methoxy-1,6-dimethylindol-3-yl)methylidene]-1H-indol-2-one
  参考文献：
  名称：

  Substituted E-3-(2-Chloro-3-indolylmethylene)1,3-dihydroindol-2-ones with Antitumor Activity. Effect on the Cell Cycle and Apoptosis

  摘要：

  The synthesis and antitumor activity of new E-3-(2-chloro-3-indolylmethylene)1,3-dihydroindol-2-ones is described. They were studied at the National Cancer Institute, taking into consideration the 50% growth inhibitory power (pGI(50)), the cytostatic effect (pTGI = total growth inhibition), and the cytotoxic effect (pLC(50)). All the compounds were potent growth inhibitors, with mean pGI(50) ranging from 5.26 to 7.72. They were also analyzed with NCI COMPARE algorithm. Further studies were dedicated to the effects on the cell cycle and apoptosis.

  DOI：

  10.1021/jm070235m
• 作为产物：
  描述：

  2-氯-5-甲氧基-6-甲基-1H-吲哚-3-甲醛 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以75%的产率得到2-chloro-5-methoxy-1,6-dimethyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Substituted E-3-(2-Chloro-3-indolylmethylene)1,3-dihydroindol-2-ones with Antitumor Activity. Effect on the Cell Cycle and Apoptosis

  摘要：

  The synthesis and antitumor activity of new E-3-(2-chloro-3-indolylmethylene)1,3-dihydroindol-2-ones is described. They were studied at the National Cancer Institute, taking into consideration the 50% growth inhibitory power (pGI(50)), the cytostatic effect (pTGI = total growth inhibition), and the cytotoxic effect (pLC(50)). All the compounds were potent growth inhibitors, with mean pGI(50) ranging from 5.26 to 7.72. They were also analyzed with NCI COMPARE algorithm. Further studies were dedicated to the effects on the cell cycle and apoptosis.

  DOI：

  10.1021/jm070235m

文献信息

• Monohydrazone Based G-Quadruplex Selective Ligands Induce DNA Damage and Genome Instability in Human Cancer Cells
  作者：Jussara Amato、Giulia Miglietta、Rita Morigi、Nunzia Iaccarino、Alessandra Locatelli、Alberto Leoni、Ettore Novellino、Bruno Pagano、Giovanni Capranico、Antonio Randazzo

  DOI：10.1021/acs.jmedchem.9b01866

  日期：2020.3.26

  Targeting G-quadruplex structures is currently viewed as a promising anticancer strategy. Searching for potent and selective G-quadruplex binders, here we describe a small series of new monohydrazone derivatives designed as analogues of a lead which was proved to stabilize G-quadruplex structures and increase R loop levels in human cancer cells. To investigate the G-quadruplex binding properties of

  目前，靶向G-四链体结构是一种有前途的抗癌策略。为了寻找有效的和选择性的G-四链体结合剂，我们在此描述了一系列新的一hydr衍生物，它们被设计为铅的类似物，被证明可以稳定G-四链体结构并增加人类癌细胞中的R环水平。在体外研究新分子的G-四链体结合特性使用端粒和癌基因启动子G-四链体形成序列进行了生物物理研究。获得的结果可以鉴定出高度选择性的G-四链体配体，该配体在人类癌细胞中进行研究后证明能够稳定G-四链体和R环，并显示出与形成微核有关的有效的细胞杀伤活性，基因组不稳定的明显迹象。
• Substituted <i>E</i>-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells
  作者：Aldo Andreani、Stefania Bellini、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Natalia Calonghi、Concettina Cappadone、Maddalena Zini、Claudio Stefanelli、Lanfranco Masotti、Robert H. Shoemaker

  DOI：10.1021/jm1007165

  日期：2010.8.12

  The synthesis of new substituted E-3-(3-indolylmethylene)-1,3-dihydroindo1-2-ones is reported. The antitumor activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. Structure activity relationships are discussed. The action of selected compounds was investigated in MCF-7 breast cancer cells. The ability of these derivatives to inhibit cellular proliferation was accompanied by increased level of p53 and its transcriptional targets p21 and Bax, interference in the cell cycle progression with cell accumulation in the G2/M phase, and activation of apoptosis.