4-((triisopropylsilyl)oxy)-1H-indole | 916574-98-6

• 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: 4-((triisopropylsilyl)oxy)-1H-indole
• 英文别名: 4-triisopropylsilyloxy-1H-indole；1H-indol-4-yloxy-tri(propan-2-yl)silane
• CAS: 916574-98-6
• 化学式: C₁₇H₂₇NOSi
• 分子量: 289.493
• InChiKey: MIHOIYXSUAROSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-((triisopropylsilyl)oxy)-1H-indole 在 4-二甲氨基吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (1-(tert-butoxycarbonyl)-4-((triisopropylsilyl)oxy)-1H-indol-2-yl)boronic acid
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of indolylindazoles as potent and selective covalent inhibitors of interleukin-2 inducible T-cell kinase (ITK)

  摘要：

  Interleukin-2 inducible T-cell kinase (ITK), a member of the Tec family of tyrosine kinases, plays an important role in T cell signaling downstream of the T-cell receptor (TCR). Herein we report the discovery of a series of indolylindazole based covalent ITK inhibitors with nanomolar inhibitory potency against ITK, good kinase selectivity and potent inhibition of the phosphorylation of PLC gamma l and ERK1/2 in living cells. A computational study provided insight into the interactions between inhibitors and Phe437 at the ATP binding pocket of ITK, suggesting that both edge-to-face pi-pi interaction and the dihedral torsion angle contribute to inhibitors' potency. Compounds 43 and 55 stood out as selective covalent inhibitors with potent cellular activity, which could be used as chemical tools for further study of ITK functions. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111918
• 作为产物：
  描述：

  4-羟基吲哚 、 三异丙基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以99%的产率得到4-((triisopropylsilyl)oxy)-1H-indole
  参考文献：
  名称：

  Efficient direct 2,2,2-trifluoroethylation of indoles via C–H functionalization

  摘要：

  无金属直接在未保护的吲哚位置3上进行三氟乙基化，通过C-H官能化呈现：直接合成和密度泛函理论研究。

  DOI：

  10.1039/c5cc00519a

文献信息

• JNK modulators
  申请人：Dunn James Patrick

  公开号：US20080146565A1

  公开（公告）日：2008-06-19

  Compounds of formula I modulate JNK: wherein the variables are as defined herein.

  式I的化合物调节JNK： 其中变量的定义如本文所述。
• Rhodium Carbenoid Approach for Introduction of 4-Substituted (<i>Z</i>)-Pent-2-enoates into Sterically Encumbered Pyrroles and Indoles
  作者：Yajing Lian、Huw M. L. Davies

  DOI：10.1021/ol9028385

  日期：2010.3.5

  An unusual rhodium carbenoid approach for introduction of 4-substituted (Z)-pent-2-enoates into sterically encumbered pyrroles and indoles is described. These studies show that (Z)-vinylcarbenoids have a greater tendency than (E)-vinylcarbenoids to react at the vinylogous position of the carbenoid rather than at the carbenoid center.

  描述了一种将 4-取代的 ( Z )-pent-2-enoates 引入空间阻碍的吡咯和吲哚中的不寻常的铑类胡萝卜素方法。这些研究表明，( Z )-乙烯基类胡萝卜素比( E )-乙烯基类胡萝卜素更倾向于在类胡萝卜素的插烯位置而不是在类胡萝卜素中心发生反应。
• Novel multicyclic compounds and the use thereof
  申请人：Chatterjee Sankar

  公开号：US20060276497A1

  公开（公告）日：2006-12-07

  The present invention is directed to novel multicyclic molecules that mediate enzymatic activity. In particular, the compounds may be effective in the treatment of diseases or disease states related to the activity of PARP, VEGFR2, and MLK3 enzymes, including, for example, neurodegenerative diseases, inflammation, ischemia, and cancer.

  本发明涉及介导酶活性的新型多环分子。特别是，这些化合物可能在治疗与PARP、VEGFR2和MLK3酶的活性相关的疾病或疾病状态方面具有有效性，包括例如神经退行性疾病、炎症、缺血和癌症。
• NOVEL MULTICYCLIC COMPOUNDS AND THE USE THEREOF
  申请人：Chatterjee Sankar

  公开号：US20110059959A1

  公开（公告）日：2011-03-10

  The present invention is directed to novel multicyclic molecules that mediate enzymatic activity. In particular, the compounds may be effective in the treatment of diseases or disease states related to the activity of PARP, VEGFR2, and MLK3 enzymes, including, for example, neurodegenerative diseases, inflammation, ischemia, and cancer.

  本发明涉及新型多环分子，可介导酶活性。特别是，这些化合物可以在治疗与PARP、VEGFR2和MLK3酶活性相关的疾病或疾病状态方面发挥作用，包括例如神经退行性疾病、炎症、缺血和癌症。
• Multicyclic compounds and the use thereof
  申请人：Chatterjee Sankar

  公开号：US08716493B2

  公开（公告）日：2014-05-06

  The present invention is directed to novel multicyclic molecules that mediate enzymatic activity. In particular, the compounds may be effective in the treatment of diseases or disease states related to the activity of PARP, VEGFR2, and MLK3 enzymes, including, for example, neurodegenerative diseases, inflammation, ischemia, and cancer.

  本发明涉及新型多环分子，其介导酶活性。特别地，这些化合物可能在治疗与PARP，VEGFR2和MLK3酶活性相关的疾病或疾病状态方面具有有效性，包括例如神经退行性疾病，炎症，缺血和癌症。