2‐(4‐hydroxyphenyl)‐1‐(4‐methoxybenzyl)‐3‐methyl‐1H‐indol‐5‐ol | 1124291-72-0

• 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‐(4‐hydroxyphenyl)‐1‐(4‐methoxybenzyl)‐3‐methyl‐1H‐indol‐5‐ol
• 英文别名: 2-(4-Hydroxyphenyl)-1-[(4-methoxyphenyl)methyl]-3-methyl-1H-indol-5-ol；2-(4-hydroxyphenyl)-1-[(4-methoxyphenyl)methyl]-3-methylindol-5-ol
• CAS: 1124291-72-0
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: GXZPCEUXWVLCPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-5-羟基-2-(4-羟基苯基)-1H-吲哚 在 aluminum (III) chloride 、 四丁基氢氧化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 2‐(4‐hydroxyphenyl)‐1‐(4‐methoxybenzyl)‐3‐methyl‐1H‐indol‐5‐ol
  参考文献：
  名称：

  Tethered indoles as functionalizable ligands for the estrogen receptor

  摘要：

  To create ligands for the estrogen receptor that contain pendant groups for tethering to a poly(amido)amine (PAMAM) dendrimer, we have explored a class of N-substituted 2-phenyl indoles. Attachment of tethers of different length and chemical nature to this non-steroidal indole scaffold gave high affinity ligand-tether conjugates that can be easily functionalized. To further explore the utility of this system, an indole-conjugated dendrimer was prepared and evaluated as an estrogen receptor ligand. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.043

文献信息

• Bazedoxifene analogs as potential WDHD1 degraders and antitumor agents: Synthesis, evaluation and molecular dynamics simulation studies
  作者：Leyuan Chen、Gaiting Liu、Fancui Meng、Yu shi、Zhennan Fang、Zhenyu Peng、Manjiang Wang、Wenfeng Gou、Wenbin Hou、Yiliang Li

  DOI：10.1002/ddr.22155

  日期：2024.2

  rate on WDHD1 in MCF7 cells at 10 μM, from the Food and Drug Administration-approved compound library. Here, we initially established the binding model of BZA, synthesized and evaluated eight BZA analogs. Further, we detailed the use of molecular dynamics simulations to provide insights into the basis for activity against WDHD1. This binding mode will be instructive for the development of new WDHD1

  DNA修复与肿瘤对放疗和化疗的抵抗力密切相关。 WD重复序列和HMG-box DNA结合蛋白1（WDHD1）是DNA同源重组修复的关键接头，其过度表达与许多肿瘤患者的不良预后有关。我们之前从食品和药物管理局批准的化合物库中鉴定并验证了巴多昔芬 (BZA)，10 μM 时，它对 MCF7 细胞中的 WDHD1 具有 60% 的抑制率。在这里，我们初步建立了BZA的结合模型，合成并评估了八种BZA类似物。此外，我们详细介绍了分子动力学模拟的使用，以深入了解针对 WDHD1 的活性基础。这种结合模式对于新型 WDHD1 降解剂的开发具有指导意义。
• Tethered indoles as functionalizable ligands for the estrogen receptor
  作者：Bridget G. Trogden、Sung Hoon Kim、Shuyi Lee、John A. Katzenellenbogen

  DOI：10.1016/j.bmcl.2008.11.043

  日期：2009.1

  To create ligands for the estrogen receptor that contain pendant groups for tethering to a poly(amido)amine (PAMAM) dendrimer, we have explored a class of N-substituted 2-phenyl indoles. Attachment of tethers of different length and chemical nature to this non-steroidal indole scaffold gave high affinity ligand-tether conjugates that can be easily functionalized. To further explore the utility of this system, an indole-conjugated dendrimer was prepared and evaluated as an estrogen receptor ligand. (C) 2008 Elsevier Ltd. All rights reserved.