3-(6-溴-3H-吲哚-3-基)-丙酸甲酯 | 210889-33-1

• 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
• 中文名称: 3-(6-溴-3H-吲哚-3-基)-丙酸甲酯
• 英文名称: 3-(6-bromo-3H-indol-3-yl)-propionic acid methyl ester
• 英文别名: ethyl 3-(6-bromo-1H-indol-3-yl)propanoate；Ethyl 3-(6-Bromo-3-indolyl)propanoate
• CAS: 210889-33-1
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: QKMGRSZMQMSDBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(6-溴-3H-吲哚-3-基)-丙酸甲酯 在 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 49.42h， 生成 N-<(3-bromo-benzylcarbamoyl)-methyl>-3-(6-bromo-3H-indol-3-yl)-propionamide
  参考文献：
  名称：

  Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin

  摘要：

  The western subunit (fused bicyclic 16+15 membered ring) was synthesized by sequential intramolecular SNAr reaction and the first 17-membered ring compound as model of the eastern subunit was obtained by an intramolecular Ni-0 mediated coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00171-4
• 作为产物：
  描述：

  3-(6-bromo-3H-indol-3-yl)-acrylic acid methyl ester 在 bismuth(III) chloride 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到3-(6-溴-3H-吲哚-3-基)-丙酸甲酯
  参考文献：
  名称：

  Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin

  摘要：

  The western subunit (fused bicyclic 16+15 membered ring) was synthesized by sequential intramolecular SNAr reaction and the first 17-membered ring compound as model of the eastern subunit was obtained by an intramolecular Ni-0 mediated coupling reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00171-4

文献信息

• Synthesis of CF₃-Containing Spirocyclic Indolines via a Red-Light-Mediated Trifluoromethylation/Dearomatization Cascade
  作者：Liangyong Mei、Jules Moutet、Savannah M. Stull、Thomas L. Gianetti

  DOI：10.1021/acs.joc.1c01313

  日期：2021.8.6

  Umemoto’s reagent has been developed. This protocol provides a facile and efficient approach for the construction of functionalized and potentially biologically important CF3-containing 3,3-spirocyclic indolines with moderate to high yields and excellent diastereoselectivities under mild conditions. The success of multiple gram-scale (1 and 10 g) experiments further highlights the robustness and practicality

  已经开发了红光介导的n Pr-DMQA +催化级联分子内三氟甲基化和吲哚衍生物与 Umemoto 试剂的脱芳构化。该协议为构建功能化且具有潜在生物学重要性的 CF 3 3,3-螺环二氢吲哚提供了一种简便有效的方法，在温和条件下具有中等至高产率和优异的非对映选择性。多个克级 (1 和 10 g) 实验的成功进一步突出了该协议的稳健性和实用性以及使用红光的优点。机理研究支持形成关键的 CF 3自由基物种和脱芳基苄基碳正离子中间体。
• Indole arylation studies directed towards the synthesis of simplified eastern subunits of chloropeptin and kistamycin
  作者：Annie-Claude Carbonnelle、Eduardo González Zamora、René Beugelmans、Georges Roussi

  DOI：10.1016/s0040-4039(98)00818-1

  日期：1998.6

  Aryl indoles which are building blocks for the synthesis of simplified analogues of macropolypeptides containing an endo carbon-carbon bond are obtained by Suzuki Pd-catalyzed cross coupling reactions involving either haloindoles or indole boronic acids and properly meta substituted phenyl components. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Discovery of aryl-substituted indole and indoline derivatives as RORγt agonists
  作者：Yan Zhu、Nannan Sun、Mingcheng Yu、Huimin Guo、Qiong Xie、Yonghui Wang

  DOI：10.1016/j.ejmech.2019.111589

  日期：2019.11

  A series of aryl-substituted indole and indoline derivatives were discovered as novel ROR gamma t agonists by a scaffold-based hybridization of the reported ROR gamma t agonists 1 and 2. SAR studies on the core structures, the RHS hydrophilic side chains and the LHS hydrophobic aryl groups of a hybrid compound 3 led to the identification of potent ROR gamma t agonists with improved drug-like properties. Compound 14 represented a high potency lead with an EC50 of 20.8 +/- 1.5 nM, the (S)-enantiomer (EC50 = 16.1 +/- 4.5 nM) of which was 17 times more potent than the (R) counterpart (EC50 = 286 +/- 30.4 nM) in ROR gamma dual FRET assay. The cell based GAL4 reporter gene assay also suggested 14 as the most active compound which exhibited an EC50 of 247 +/- 33.1 nM and a maximum activation percentage of 133%. Moreover, 14 showed high metabolic stability (t(1/2) = 113 min) in mouse liver microsome and had improved aqueous solubility at pH 7.4 compared to the parent compounds. Furthermore, 14 was found to be orally bioavailable and demonstrated excellent in vivo pharmacokinetics in mice. Present studies indicate that 14 deserves further investigation in tumor animal models as a potential candidate of ROR gamma t agonist for cancer immunotherapy. (C) 2019 Elsevier Masson SAS. All rights reserved.