5-羟基吲哚-3-乙腈 | 100929-86-0

• 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: 5-羟基吲哚-3-乙腈
• 英文名称: 2-(5-hydroxy-1H-indol-3-yl)acetonitrile
• CAS: 100929-86-0
• 化学式: C₁₀H₈N₂O
• 分子量: 172.186
• InChiKey: SHKJOZJRCTYYNW-UHFFFAOYSA-N

物化性质

• 沸点：
  455.7±30.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.8
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-羟基吲哚-3-乙腈 在 sodium methylate 、 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.83h， 生成 (Z)-2-(5-(3-(pyrrolidin-1-yl)propoxy)-1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile
  参考文献：
  名称：

  Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

  摘要：

  Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI(50) 1.5 mu M). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.011
• 作为产物：
  描述：

  5-苄氧基吲哚-3-乙腈 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以84%的产率得到5-羟基吲哚-3-乙腈
  参考文献：
  名称：

  [EN] SELECTIVE ANTI-CANCER COMPOUNDS
  [FR] COMPOSÉS ANTI-CANCÉREUX SÉLECTIFS

  摘要：

  式I的化合物，其中该化合物具有以下结构：其中R1至R5，Y，L，Z和X1至X7的含义如描述中所示，这些化合物在治疗过度增殖性疾病方面具有用途。

  公开号：

  WO2016200339A1

文献信息

• USEFUL INDOLE COMPOUNDS
  申请人：Bartolini Wilmin

  公开号：US20090264653A1

  公开（公告）日：2009-10-22

  Indoles that have activity as inhibitors of FAAH are described as are indoles and indole derivatives that have activity as inhibitors of DAO.

  本文描述了具有FAAH抑制剂活性的吲哚化合物，以及具有DAO抑制剂活性的吲哚及其衍生物。
• Positive modulators of nicotinic receptor agonists
  申请人：AstraZeneca AB

  公开号：US06750242B1

  公开（公告）日：2004-06-15

  Compounds of Formula I wherein R1, R2, R3 and R4 are as defined in the specification, enantiomers thereof, pharmaceutically acceptable salts thereof, processes for preparing them, pharmaceutical compositions containing them and their use in therapy, especially for treatment of conditions associated with reductions in nicotinic transmission. The compounds of the invention enhance the efficacy of agonists at nicotinic receptors.

  本发明的化合物I式中，其中R1、R2、R3和R4的定义如规范中所述，其对映异构体，其药学上可接受的盐，制备它们的方法，包含它们的制药组合物以及它们在治疗中的应用，特别是用于治疗与尼古丁传递减少有关的疾病。本发明的化合物增强了尼古丁受体激动剂的功效。
• INDOLE COMPOUNDS
  申请人：Talley John Jeffrey

  公开号：US20100197708A1

  公开（公告）日：2010-08-05

  Indole derivatives that are useful for treating pain, inflammation and other conditions are described. Certain of the compounds are benzyl derivatives and others are benzoyl derivatives. The compounds are substituted at least at the 3 position of the indole.

  本文介绍了用于治疗疼痛、炎症和其他疾病的吲哚衍生物。其中某些化合物是苄基衍生物，而其他化合物是苯甲酰基衍生物。这些化合物至少在吲哚的3位被取代。
• Indole compounds
  申请人：Ironwood Pharmaceuticals, Inc.

  公开号：EP2610244A1

  公开（公告）日：2013-07-03

  Indole derivatives of formula A that are useful for treating pain, inflammation and other conditions are described. Certain of the compounds are benzyl derivatives and others are benzoyl derivatives. The compounds are substituted at least at the 3 position of the indole.

  描述了可用于治疗疼痛、炎症和其他病症的式 A 的吲哚衍生物。其中一些化合物是苄基衍生物，另一些则是苯甲酰基衍生物。这些化合物至少在吲哚的 3 位被取代。
• Selective anti-cancer compounds
  申请人：NATIONAL UNIVERSITY OF SINGAPORE

  公开号：US10308631B2

  公开（公告）日：2019-06-04

  A compound of formula I, wherein the compound of formula I has the structure: wherein R1 to R5, Y, L, Z and X1 to X7 have meanings given in the description, said compounds having utility in the treatment of hyperproliferative disease.

  一种式 I 的化合物，其中式 I 的化合物具有如下结构： 其中 R1 至 R5、Y、L、Z 和 X1 至 X7 的含义如描述中所给出，所述化合物在治疗过度增殖性疾病中具有实用性。