tert-butyl (3-(1H-indol-3-yl)propyl)carbamate | 110317-45-8

• 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: tert-butyl (3-(1H-indol-3-yl)propyl)carbamate
• 英文别名: [3-(1H-lndol-3-yl)-propyl]-carbamic acid tert-butyl ester；tert-butyl N-[3-(1H-indol-3-yl)propyl]carbamate
• CAS: 110317-45-8
• 化学式: C₁₆H₂₂N₂O₂
• 分子量: 274.363
• InChiKey: FHMNZEJOGNXXDA-UHFFFAOYSA-N

物化性质

• 沸点：
  458.6±28.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-(1H-indol-3-yl)propyl)carbamate 在 二甲基硫 、 氧气 、 rose bengal 作用下， 生成 1-(tert-Butyloxycarbonyl)-2,3,4,4a,9,9a-hexahydro-1H-pyrido<2,3-b>indol-4a-ol
  参考文献：
  名称：

  Droste, Holger; Wieland, Theodor, Liebigs Annalen der Chemie, 1987, p. 901 - 910

  摘要：

  DOI：
• 作为产物：
  描述：

  吲哚-3-丙酰胺 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 tert-butyl (3-(1H-indol-3-yl)propyl)carbamate
  参考文献：
  名称：

  高价碘介导的同色胺衍生物的环化

  摘要：

  已经建立了使用高价碘（1-氯-1,2-二甲基吡啶）构建4a-氯四氢吡啶并[2,3-b]吲哚和3,3-螺环3 H-吲哚的简便高效的环类胺及其衍生物的环化方法。苯并三唑-3-酮）在温和的条件下使用。广泛的基体范围和成功的克级实验为这种无金属的转化提供了进一步应用的巨大潜力。

  DOI：

  10.1002/ejoc.201801842

文献信息

• A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents
  作者：Xiaofeng Ma、Joshua J. Farndon、Tom A. Young、Natalie Fey、John F. Bower

  DOI：10.1002/anie.201708176

  日期：2017.11.13

  A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

  概述了具有广泛范围的 CN 键形成脱芳构化方案。具体来说，双功能氨基试剂用于顺序亲核和亲电CN键形成，后者影响关键的脱芳构化步骤。使用这种方法，只需两到三个步骤即可将 γ-芳基化醇转化为各种差异保护的螺环吡咯烷。
• Aryl–indolyl maleimides as inhibitors of CaMKIIδ. Part 3: Importance of the indole orientation
  作者：Qing Lu、Zheng Chen、John Perumattam、Dan-Xiong Wang、Weiling Liang、Yong-jin Xu、Steven Do、Llorente Bonaga、Jeffrey Higaki、Hanmin Dong、Albert Liclican、Steve Sideris、Maureen Laney、Sundeep Dugar、Babu Mavunkel、Daniel E. Levy

  DOI：10.1016/j.bmcl.2008.02.057

  日期：2008.4

  A family of aryl-substituted maleimides was prepared and studied for their activity against calmodulin dependant kinase. Inhibitory activities against the enzyme ranged from 10 nM to > 20 mu M and were dependant upon both the nature of the aryl group and the tether joining the basic amine to the indolyl maleimide core of the inhibitors. Key interactions with the kinase ATP site and hinge region, predicted by homology modeling, were confirmed. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of an Indazole-Based Selective Protein Arginine Deiminase 4 (PAD4) Inhibitor
  作者：Caroline Chandra Tjin、Rebecca F. Wissner、Haya Jamali、Alanna Schepartz、Jonathan A. Ellman

  DOI：10.1021/acsmedchemlett.8b00283

  日期：2018.10.11

  Protein arginine deiminase 4 (PAD4) is a calcium-dependent enzyme that catalyzes the conversion of arginine to citrulline within target proteins. Dysregulation of PAD4 has been implicated in a number of human diseases, including rheumatoid arthritis and other inflammatory diseases as well as cancer. In this study, we report on the design, synthesis, and evaluation of a new class of haloacetamidine-based compounds as potential PAD4 inhibitors. Specifically, we describe the identification of 4,5,6-trichloroindazole 24 as a highly potent PAD4 inhibitor that displays >10-fold selectivity for PAD4 over PAD3 and >50-fold over PAD1 and PAD2. The efficacy of this compound in cells was determined by measuring the inhibition of PAD4-mediated H4 citrullination in HL-60 granulocytes.
• NEW COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1071683A1

  公开（公告）日：2001-01-31
• [EN] NEW COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES
  申请人：ASTRAZENECA AB

  公开号：WO1999046264A1

  公开（公告）日：1999-09-16

  (EN) The present invention provides inhibitors of protein kinase C, of formula (I), wherein: one of: R1 and R2, R2 and R3 or R3 and R4, together form a 5 or 6 membered ring and the two groups of R1, R2, R3 and R4 not forming a ring, are H; and salts thereof, formulations comprising said inhibitors of protein kinase C of formula (I), processes for preparation thereof and use thereof in the manufacture of a medicament for the treatment of inflammatory, immunological, bronchopulmonary, cardiovascular, oncological or CNS-degenerative disorders.(FR) La présente invention concerne des inhibiteurs de la protéine kinase C de formule (I), dans laquelle un des groupes R1 et R2, R2 et R3, ou R3 et R4 forment ensemble un cycle à 5 ou 6 chaînons, et dans laquelle les deux groupes de R1, R2, R3, et R4 ne formant pas de cycle représentent H. L'invention concerne également leurs sels, des formulations comprenant lesdits inhibiteurs de la protéine kinase C de formule (I), leurs procédés de préparation et leur utilisation dans la production d'un médicament destiné au traitement de troubles inflammatoires, immunologiques, broncho-pulmonaires, cardio-vasculaires ou oncologiques, ou de maladies dégénératives du SNC.