2-chloro-5-(dimethylamino)indole-3-carbaldehyde | 1237738-69-0

• 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-(dimethylamino)indole-3-carbaldehyde
• 英文别名: 2-chloro-5-(dimethylamino)-1H-indole-3-carbaldehyde
• CAS: 1237738-69-0
• 化学式: C₁₁H₁₁ClN₂O
• 分子量: 222.674
• InChiKey: ASJPTJNJDWTNPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-2-氧化吲哚 、 2-chloro-5-(dimethylamino)indole-3-carbaldehyde 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 (3E)-4-chloro-3-[[2-chloro-5-(dimethylamino)-1H-indol-3-yl]methylidene]-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：

  5-(dimethylamino)-3-[(dimethylamino)methylene]-2-oxoindoline-1-carbaldehyde 在 三氯氧磷 作用下， 反应 0.25h， 以30%的产率得到2-chloro-5-(dimethylamino)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

• Identification of a new bisindolinone arresting IGROV1 cells proliferation
  作者：Rita Morigi、Chiara Zalambani、Giovanna Farruggia、Laura Verardi、Daniele Esposito、Alberto Leoni、Francesca Borsetti、Manuela Voltattorni、Laura Zambonin、Luca Pincigher、Natalia Calonghi、Alessandra Locatelli

  DOI：10.1016/j.ejmech.2024.116365

  日期：2024.5

  were submitted to the National Cancer Institute for evaluation of antitumor activity in human cell lines. In particular, compound showed remarkable selectivity against IGROV1, an ovarian cancer cell line, without affecting healthy human fibroblast cells. Analyses of cytotoxicity, cell proliferation, cell migration, epigenetic changes, gene expression, and DNA damage were performed to obtain detailed

  在初步筛选中，一系列新型 Knoevenagel 加合物被提交给国家癌症研究所，用于评估人类细胞系的抗肿瘤活性。特别是，该化合物对 IGROV1（一种卵巢癌细胞系）表现出显着的选择性，而不影响健康的人类成纤维细胞。对细胞毒性、细胞增殖、细胞迁移、表观遗传变化、基因表达和 DNA 损伤进行分析，以获得有关其抗肿瘤特性的详细信息。我们的结果表明，它会导致增殖停滞、运动性降低、组蛋白过度乙酰化、细胞周期蛋白 D1 和整合素 β1 基因转录的 α5 亚基下调。此外，治疗会降低细胞周期蛋白 D1 的转录物和蛋白水平，从而增加对电离辐射的敏感性，并导致与细胞周期蛋白 D1 基因沉默相当的 DNA 损伤。
• 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.