5-bromo-1-(4-methoxybenzyl)-1H-indole-3-carboxaldehyde | 1207615-59-5

• 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: 5-bromo-1-(4-methoxybenzyl)-1H-indole-3-carboxaldehyde
• CAS: 1207615-59-5
• 化学式: C₁₇H₁₄BrNO₂
• 分子量: 344.208
• InChiKey: INWJHOATXMZLIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromo-1-(4-methoxybenzyl)-1H-indole-3-carboxaldehyde 在 三溴化硼 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.33h， 生成 5-bromo-1-(4-(3-(piperidin-1-yl)propoxy)benzyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  发现靶向糖蛋白130的巴多昔芬类似物。

  摘要：

  GP130在信号转导中的失调涉及多种类型的人类疾病，尤其是癌症，这表明GP130是癌症治疗的诱人靶标。然而，常规上将GP130视为不可消耗的靶标，因此GP130 PPI抑制剂的发现极具挑战性。借助基于结构的药物设计，在这项研究中，设计了两个系列的基于巴多昔芬的类似物，靶向GP130 D1域并阻断IL-6 / GP130 / STAT3信号通路进行抗肿瘤治疗。这些设计的化合物大多数都显示出对癌细胞有效的抗增殖活性。代表性的化合物10a通过SPR和DARTS方法均以3.8μM的亲和力（KD）值直接结合GP130蛋白。后来，分子对接研究预测10a靶向GP130的D1结构域和co-IP分析表明10a不抑制IL-6R / GP130相互作用，这意味着10a不结合GP130的D2和D3结构域。此外，10a选择性抑制JAK2和STAT3磷酸化以及IL-6诱导的STAT3磷酸化。10a有效抑制肿瘤细胞的活

  DOI：

  10.1016/j.ejmech.2020.112375
• 作为产物：
  描述：

  5-溴吲哚-3-甲醛 、 4-甲氧基溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88 %的产率得到5-bromo-1-(4-methoxybenzyl)-1H-indole-3-carboxaldehyde
  参考文献：
  名称：

  发现靶向糖蛋白130的巴多昔芬类似物。

  摘要：

  GP130在信号转导中的失调涉及多种类型的人类疾病，尤其是癌症，这表明GP130是癌症治疗的诱人靶标。然而，常规上将GP130视为不可消耗的靶标，因此GP130 PPI抑制剂的发现极具挑战性。借助基于结构的药物设计，在这项研究中，设计了两个系列的基于巴多昔芬的类似物，靶向GP130 D1域并阻断IL-6 / GP130 / STAT3信号通路进行抗肿瘤治疗。这些设计的化合物大多数都显示出对癌细胞有效的抗增殖活性。代表性的化合物10a通过SPR和DARTS方法均以3.8μM的亲和力（KD）值直接结合GP130蛋白。后来，分子对接研究预测10a靶向GP130的D1结构域和co-IP分析表明10a不抑制IL-6R / GP130相互作用，这意味着10a不结合GP130的D2和D3结构域。此外，10a选择性抑制JAK2和STAT3磷酸化以及IL-6诱导的STAT3磷酸化。10a有效抑制肿瘤细胞的活

  DOI：

  10.1016/j.ejmech.2020.112375

文献信息

• Novel substituted (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents
  作者：Y. Thirupathi Reddy、Konjeti R. Sekhar、Nidhish Sasi、P. Narsimha Reddy、Michael L. Freeman、Peter A. Crooks

  DOI：10.1016/j.bmcl.2009.11.082

  日期：2010.1

  A series of (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-dione (9a-9m) and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione (10a-10i) derivatives that incorporate a variety of aromatic substituents in both the indole and N-benzyl moieties have been synthesized. These analogs were evaluated for their radiosensitization activity against the HT-29 cell line. Three analogs, 10a, 10b, and 10c were identified as the most potent radiosensitizing agents. (C) 2009 Elsevier Ltd. All rights reserved.
• Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones
  作者：Y. Thirupathi Reddy、P. Narsimha Reddy、Srinivas Koduru、Chendil Damodaran、Peter A. Crooks

  DOI：10.1016/j.bmc.2010.03.054

  日期：2010.5

  A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione ( 3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC50 values of 4.4 and 5.2 mu M, respectively, compared to 5-fluorouracil (IC50 = 15.2 mu M) against MCF-7 cells. (C) 2010 Elsevier Ltd. All rights reserved.
• Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines
  作者：Narsimha Reddy Penthala、Thirupathi Reddy Yerramreddy、Peter A. Crooks

  DOI：10.1016/j.bmcl.2009.11.083

  日期：2010.1

  The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. The analogs 3a, 3b, 3d-3g, 3k and 3l were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC50 values < 10 mu M for 30% of the cell lines in the panel. Compound 3e was an effective inhibitor of leukemia, CNS, melanoma, and breast cancer cell growth, but generally less effective as a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization. (C) 2009 Elsevier Ltd. All rights reserved.