ethyl 2-(6-bromo-1H-indol-1-yl)acetate | 281204-54-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(6-bromo-1H-indol-1-yl)acetate
• 英文别名: ethyl 2-(6-bromoindol-1-yl)acetate
• CAS: 281204-54-4
• 化学式: C₁₂H₁₂BrNO₂
• 分子量: 282.137
• InChiKey: ZMDSHPGQZDXPLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 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：

  ethyl 2-(6-bromo-1H-indol-1-yl)acetate 在 sodium acetate 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 6-Bromo-1-[2-(1,4-diazepan-1-yl)ethyl]indole
  参考文献：
  名称：

  1-(Bicyclopiperazinyl)ethylindoles and 1-(homopiperazinyl)ethyl-indoles as highly selective and potent 5-HT7 receptor ligands

  摘要：

  A novel series of 1-(bicyclopiperazinyl)ethylindole and 1-(homopiperazinyl)ethyl-indole derivatives was synthesized and found to be potent and selective 5-HT7 receptor ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00438-9
• 作为产物：
  描述：

  6-溴吲哚 、 氯乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以78%的产率得到ethyl 2-(6-bromo-1H-indol-1-yl)acetate
  参考文献：
  名称：

  氨基酸衍生物，VIII [1]：带有吲哚侧链的α-氨基酸酯的合成和抗菌性评估

  摘要：

  合成了与吲哚残基缀合的一系列肽和二肽衍生物。测试了所制备的化合物对两种不同的细菌和一种显示不同程度的抗微生物活性或抑制作用的抗真菌物种的抗微生物活性。

  DOI：

  10.1007/s00706-008-0891-7

文献信息

• [EN] NOVEL SMALL MOLECULE INHIBITORS OF TEAD TRANSCRIPTION FACTORS<br/>[FR] NOUVEAUX INHIBITEURS À PETITES MOLÉCULES DE FACTEURS DE TRANSCRIPTION TEAD
  申请人：MASSACHUSETTS GEN HOSPITAL

  公开号：WO2020190774A1

  公开（公告）日：2020-09-24

  The present disclosure compounds, as well as their compositions and methods of use. The compounds inhibit the activity of the TEAD transcription factor, and are useful in the treatment of diseases related to the activity of TEAD transcription factor including, e.g., cancer and other diseases.

  本公开涉及化合物及其组合物和使用方法。这些化合物抑制TEAD转录因子的活性，并可用于治疗与TEAD转录因子活性相关的疾病，例如癌症和其他疾病。
• Virtual Screening and Structure-Based Discovery of Indole Acylguanidines as Potent β-secretase (BACE1) Inhibitors
  作者：Yiquan Zou、Li Li、Wuyan Chen、Tiantian Chen、Lanping Ma、Xin Wang、Bing Xiong、Yechun Xu、Jingkang Shen

  DOI：10.3390/molecules18055706

  日期：——

  cleavage of amyloid precursor protein by β-secretase (BACE1) is a key step in generating the N-terminal of β-amyloid (Aβ), which further forms into amyloid plaques that are considered as the hallmark of Alzheimer's disease. Inhibitors of BACE1 can reduce the levels of Aβ and thus have a therapeutic potential for treating the disease. We report here the identification of a series of small molecules bearing

  β-分泌酶 (BACE1) 对淀粉样前体蛋白进行蛋白水解切割是生成 β-淀粉样蛋白 (Aβ) 的 N 端的关键步骤，其进一步形成被认为是阿尔茨海默病标志的淀粉样斑块。BACE1 抑制剂可以降低 Aβ 的水平，因此具有治疗该疾病的治疗潜力。我们在这里报告了一系列带有吲哚酰基胍核心结构的小分子作为有效的 BACE1 抑制剂的鉴定。最初的弱片段是通过虚拟筛选发现的，然后进行了先导优化。借助已发现的两种抑制剂（化合物 19 和 25）与 BACE1 的共晶结构，我们探索了吲哚和芳基周围的 SAR，并获得了几种 BACE1 抑制剂，其效力比最初命中的片段强约 1,000 倍。
• Design, synthesis and biological activity of novel dimethyl-{2-[6-substituted-indol-1-yl]-ethyl}-amine as potent, selective, and orally-Bioavailable 5-HT 1D agonists
  作者：Methvin Isaac、Malik Slassi、Tao Xin、Jalaj Arora、Anne O'Brien、Louise Edwards、Neil MacLean、Julie Wilson、Lidia Demschyshyn、Phillipe Labrie、Angela Naismith、Shawn Maddaford、Damon Papac、Shuree Harrison、Hua Wang、Stan Draper、Ashok Tehim

  DOI：10.1016/j.bmcl.2003.09.025

  日期：2003.12

  A novel series of highly potent human 5-HT1D agonists, dimethyl-2-[6-substituted-indol-1-yl]-ethyl}-amine, was synthesized. Structure-activity relationship (SAR) investigation revealed 4-[1-(2-dimethylamino-ethyl)-1H-indol-6-yl]-tetrahydro-thiopyran-4-ol, 11b (ALX-2732), as a potent (K-i = 2.4 nM) agonist at the human 5-HT1D receptor with good selectivity over the other serotonin receptor subtypes. This compound demonstrated favorable in vitro metabolic stability in human and rat liver microsomes and was found to be orally bioavailable in rats (F-po = 51%) (C) 2003 Elsevier Ltd. All rights reserved.
• 1-(Bicyclopiperazinyl)ethylindoles and 1-(homopiperazinyl)ethyl-indoles as highly selective and potent 5-HT7 receptor ligands
  作者：Methvin B Isaac、Tao Xin、Anne O'Brien、David St-Martin、Angela Naismith、Neil MacLean、Julie Wilson、Lidia Demchyshyn、Ashok Tehim、Abdelmalik Slassi

  DOI：10.1016/s0960-894x(02)00438-9

  日期：2002.9

  A novel series of 1-(bicyclopiperazinyl)ethylindole and 1-(homopiperazinyl)ethyl-indole derivatives was synthesized and found to be potent and selective 5-HT7 receptor ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Amino acid derivatives, VIII [1]: synthesis and antimicrobial evaluation of α-amino acid esters bearing an indole side chain
  作者：Adel A.-H. Abdel-Rahman、Wael A. El-Sayed、Hamed M. Abdel-Bary、Ahmed E.-S. Abdel-Megied、Emad M. I. Morcy

  DOI：10.1007/s00706-008-0891-7

  日期：2008.9

  A series of peptide and dipeptide derivatives conjugated with an indole residue were synthesized. The prepared compounds were tested for antimicrobial activity against two different bacterial and one antifungal species displaying different degrees of antimicrobial activities or inhibitory actions.

  合成了与吲哚残基缀合的一系列肽和二肽衍生物。测试了所制备的化合物对两种不同的细菌和一种显示不同程度的抗微生物活性或抑制作用的抗真菌物种的抗微生物活性。