2-chloro-1H-benzo[g]indole-3-carbaldehyde | 535923-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-1H-benzo[g]indole-3-carbaldehyde
• CAS: 535923-48-9
• 化学式: C₁₃H₈ClNO
• 分子量: 229.666
• InChiKey: HGZFBKHNTUAWQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-氟吲哚-2-酮 、 2-chloro-1H-benzo[g]indole-3-carbaldehyde 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 生成 (3E)-3-[(2-chloro-1H-benzo[g]indol-3-yl)methylidene]-5-fluoro-1H-indol-2-one
  参考文献：
  名称：

  Substituted E-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells

  摘要：

  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.

  DOI：

  10.1021/jm1007165
• 作为产物：
  描述：

  1,3-二氢-2H-苯并[g]吲哚-2-酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 2-chloro-1H-benzo[g]indole-3-carbaldehyde
  参考文献：
  名称：

  Substituted E-3-(3-Indolylmethylene)-1,3-dihydroindol-2-ones with Antitumor Activity. In Depth Study of the Effect on Growth of Breast Cancer Cells

  摘要：

  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.

  DOI：

  10.1021/jm1007165

文献信息

• Synthesis and Biological Evaluation of New Bis-Indolinone Derivatives Endowed with Cytotoxic Activity
  作者：Rita Morigi、Elena Catanzaro、Alessandra Locatelli、Cinzia Calcabrini、Valentina Pellicioni、Alberto Leoni、Carmela Fimognari

  DOI：10.3390/molecules26206277

  日期：——

  A series of new Knoevenagel adducts, bearing two indolinone systems, has been synthesized and evaluated on 60 human cancer cell lines according to protocols available at the National Cancer Institute (Bethesda, MD, USA). Some derivatives proved to be potent antiproliferative agents, showing GI50 values in the submicromolar range. Compound 5b emerged as the most active and was further studied in Jurkat

  根据美国国家癌症研究所（美国马里兰州贝塞斯达）提供的方案，已经在 60 种人类癌细胞系上合成并评估了一系列带有两个吲哚酮系统的新型 Knoevenagel 加合物。一些衍生物被证明是有效的抗增殖剂，其 GI 50值在亚微摩尔范围内。化合物5b是最活跃的，并在 Jurkat 细胞中进行了进一步研究，以确定对细胞周期阶段的影响和诱导的细胞死亡类型。最后，还分析了化合物5b诱导的氧化应激和 DNA 损伤。
• Substituted E-3-(3-indolylmethylene)1,3-dihydroindol-2-ones with antiproliferative activity. Study of the effects on HL-60 leukemia cells
  作者：Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Concettina Cappadone、Giovanna Farruggia、Stefano Iotti、Lucia Merolle、Maddalena Zini、Claudio Stefanelli

  DOI：10.1016/j.ejmech.2014.04.004

  日期：2014.5

  The synthesis of new substituted E-3-(3-indolylmethylene)1,3-dihydroindol-2-ones is reported. The antiproliferative activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of the most active compound 10 was further investigated in HL-60 leukemia cells. Results obtained show that it causes a block in cell cycle progression, with cell arrest in the G2/M phase, associated with activation of apoptosis accompanied with increased oxidative stress and deregulation of the homeostasis of divalent cations, with significant increase in the cellular concentrations of free Ca2+ and Mg2+. (C) 2014 Elsevier Masson SAS. All rights reserved.
• 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.