3-bromo-5-methoxy-2-methyl-1H-indole | 883141-55-7

• 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: 3-bromo-5-methoxy-2-methyl-1H-indole
• CAS: 883141-55-7
• 化学式: C₁₀H₁₀BrNO
• 分子量: 240.099
• InChiKey: HJPRTJJLDXWGEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3-bromo-5-methoxy-2-methyl-1H-indole 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.67h， 生成 5-methoxy-1,2-dimethyl-3-(perfluorocyclopent-1-enyl)-1H-indole
  参考文献：
  名称：

  二芳杂环取代的六氟环戊烯类光致变色化合物的制备方法

  摘要：

  本发明二芳杂环取代的六氟环戊烯类光致变色化合物的制备方法，涉及有机光致变色材料，步骤是：第一步，5‑甲基‑4‑溴‑2‑噻吩甲醛缩二乙醇的合成；第二步，1,2‑二甲基‑5‑R1‑3‑溴吲哚的合成；第三步，二芳杂环取代的六氟环戊烯类光致变色化合物的合成。所制得的光致变色化合物的吸收波长红移达到50～100nm，是热不可逆的双稳态，在光信息存储、防伪识别、隐蔽材料和军事伪装材料方面均能得到应用。

  公开号：

  CN109721593A
• 作为产物：
  描述：

  5-甲氧基-2-甲基吲哚 在 N-溴代丁二酰亚胺(NBS) 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到3-bromo-5-methoxy-2-methyl-1H-indole
  参考文献：
  名称：

  新型萘并[ a ]咔唑和苯并[ c ]咔唑的简明合成

  摘要：

  从简单的吲哚前体开始，描述了萘并[ a ]咔唑和苯并[ c ]咔唑的合成。关键步骤包括使用Suzuki-Miyaura反应提供2-或3-芳基取代的吲哚，以及叔丁醇钾和光辅助的芳香环形成反应。

  DOI：

  10.1016/j.tet.2006.01.012

文献信息

• The Synthesis of Naphtho[<i>a</i>]carbazoles and Benzo[<i>c</i>]carbazoles
  作者：Charles B. de Koning、Joseph P. Michael、Johanna M. Nhlapo、Rakhi Pathak、Willem A. van Otterlo

  DOI：10.1055/s-2003-38352

  日期：——

  The synthesis of naphtho[a]carbazoles and benzo[c]carbazoles from indole precursors using a reaction mediated by potassium? -butoxide and light is described. The indole precursors were prepared utilizing Suzuki coupling methodology.

  使用钾介导的反应从吲哚前体合成萘并[a]咔唑和苯并[c]咔唑？-丁醇盐和光被描述。使用 Suzuki 偶联方法制备吲哚前体。
• Tetravalent Spiroselenurane Catalysts: Intramolecular Se···N Chalcogen Bond-Driven Catalytic Disproportionation of H₂O₂ to H₂O and O₂ and Activation of I₂ and NBS
  作者：Monojit Batabyal、Aditya Upadhyay、Rahul Kadu、Nihal Chaitanya Birudukota、Deepak Chopra、Sangit Kumar

  DOI：10.1021/acs.inorgchem.2c00651

  日期：2022.6.13

  spiroselenuranes have been explored as catalysts in synthetic oxidation iodolactonization and bromination of arenes. The synthesized spiroselenurane has activated I2 toward the iodolactonization of alkenoic acids under base-free conditions. Similarly, efficient chemo- and regioselective monobromination of various arenes with NBS catalyzed by chalcogen-bonded synthesized spiroselenuranes has been achieved

  硫属元素键相互作用最近在合成化学、结构和键合领域引起了相当大的关注。在这里，通过氧化衍生自 8-氨基喹啉的相应双(2-苯甲酰胺) 硒化物，分离了三种有机螺硒脲，它们的 Se(IV) 中心具有强烈的分子内 Se···N 硫属元素键合相互作用配体。此外，合成的螺硒醚，在测定其抗氧化活性时，首次显示出过氧化氢歧化为 H 2 O 和 O 2 ，​​由1监测的任何有机硒分子对 H 2 O 2具有一级动力学。核磁共振氢谱。供电子 5-甲硫基苯甲酰胺环取代的螺硒醚以 15.6 ± 0.4 × 10 3 μM min –1的高速率歧化过氧化氢，速率常数为 8.57 ± 0.50 × 10 –3 s –1，而 5-甲氧基和未取代的苯甲酰胺螺硒脲以 7.9 ± 0.3 × 10 3和 2.9 ± 0.3 × 10 3 μM min –1的速率催化 H 2 O 2歧化，速率常数为 1.16 ± 0.02 × 10
• Discovery of Isoquinolinone Indole Acetic Acids as Antagonists of Chemoattractant Receptor Homologous Molecule Expressed on Th2 Cells (CRTH2) for the Treatment of Allergic Inflammatory Diseases
  作者：Neelu Kaila、Bruce Follows、Louis Leung、Jennifer Thomason、Adrian Huang、Alessandro Moretto、Kristin Janz、Michael Lowe、Tarek S. Mansour、Cedric Hubeau、Karen Page、Paul Morgan、Susan Fish、Xin Xu、Cara Williams、Eddine Saiah

  DOI：10.1021/jm401509e

  日期：2014.2.27

  Previously we reported the discovery of CRA-898 (1), a diazine indole acetic acid containing CRTH2 antagonist. This compound had good in vitro and in vivo potency, low rates of metabolism, moderate permeability, and good oral bioavailability in rodents. However, it showed low oral exposure in nonrodent safety species (dogs and monkeys). In the current paper, we wish to report our efforts to understand and improve the poor PK in nonrodents and development of a new isoquinolinone subseries that led to identification of a new development candidate, CRA-680 (44). This compound was efficacious in both a house dust mouse model of allergic lung inflammation (40 mg/kg qd) as well as a guinea pig allergen challenge model of lung inflammation (20 mg/kg bid).
• Identification and Optimization of Mechanism-Based Fluoroallylamine Inhibitors of Lysyl Oxidase-like 2/3
  作者：Alison D. Findlay、Jonathan S. Foot、Alberto Buson、Mandar Deodhar、Andrew G. Jarnicki、Philip M. Hansbro、Gang Liu、Heidi Schilter、Craig I. Turner、Wenbin Zhou、Wolfgang Jarolimek

  DOI：10.1021/acs.jmedchem.9b01283

  日期：2019.11.14

  Lysyl oxidase-like 2 (LOXL2) is a secreted enzyme that catalyzes the formation of cross-links in extracellular matrix proteins, namely, collagen and elastin, and is indicated in fibrotic diseases. Herein, we report the identification and subsequent optimization of a series of indole-based fluoroallylamine inhibitors of LOXL2. The result of this medicinal chemistry campaign is PXS-5120A (12k), a potent, irreversible inhibitor that is >300-fold selective for LOXL2 over LOX. PXS-5120A also shows potent inhibition of LOXL3, an emerging therapeutic target for lung fibrosis. Key to the development of this compound was the utilization of a compound oxidation assay. PXS-5120A was optimized to show negligible substrate activity in vitro for related amine oxidase family members, leading to metabolic stability. PXS-5120A, in a pro-drug form (PXS-5129A, 12o), displayed anti-fibrotic activity in models of liver and lung fibrosis, thus confirming LOXL2 as an important target in diseases where collagen cross-linking is implicated.