5-amino-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 58372-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-amino-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 5-amino-2-(2-hydroxy-ethyl)-benzo[de]isoquinoline-1,3-dione；3-Amino-1,8-naphthal-(N-β-hydroxyethyl)imid；5-Amino-2-(2-hydroxyethyl)benzo[de]isoquinoline-1,3-dione
• CAS: 58372-01-3
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: GCHBBBSDJOQWQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-羟基-乙基)-5-硝基-苯并[去]异喹啉-1,3-二酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以74%的产率得到5-amino-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Small Molecule Modifiers of MicroRNA miR-122 Function for the Treatment of Hepatitis C Virus Infection and Hepatocellular Carcinoma

  摘要：

  MicroRNAs are a recently discovered new class of important endogenous regulators of gene function. Aberrant regulation of microRNAs has been linked to various human diseases, most importantly cancer. Small molecule intervention of microRNA misregulation has the potential to provide new therapeutic approaches to such diseases. Here, we report the first small molecule inhibitors and activators of the liver-specific microRNA miR-122. This microRNA is the most abundant microRNA in the liver and is involved in hepatocellular carcinoma development and hepatitis C virus (HCV) infection. Our small molecule inhibitors reduce viral replication in liver cells and represent a new approach to the treatment of HCV infections. Moreover, small molecule activation of miR-122 in liver cancer cells selectively induced apoptosis through caspase activation, thus having implications in cancer chemotherapy. In addition to providing a new approach for the development of therapeutics, small molecule modifiers of miR-122 function are unique tools for exploring miR-122 biogenesis.

  DOI：

  10.1021/ja910275u

文献信息

• Ionic liquids accelerate access to N-substituted-1,8-naphthalimides
  作者：Kylie A. MacGregor、Adam McCluskey

  DOI：10.1016/j.tetlet.2010.12.015

  日期：2011.2

  The synthesis of N-substituted-1,8-naphthalimides is accelerated in the presence of the room temperature ionic liquid [BMIM][NO(3)]. Reaction times are reduced from 18 h in volatile organic compounds (VOCs) (PhCH(3), EtOH and THF) to 20 min in the ionic liquid [BMIM][NO(3)]. The reaction yields are typically increased to >85% and the products are isolated by ethanol-mediated precipitation direct from the ionic liquid, requiring no further purification. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Small Molecule Modifiers of MicroRNA miR-122 Function for the Treatment of Hepatitis C Virus Infection and Hepatocellular Carcinoma
  作者：Douglas D. Young、Colleen M. Connelly、Christoph Grohmann、Alexander Deiters

  DOI：10.1021/ja910275u

  日期：2010.6.16

  MicroRNAs are a recently discovered new class of important endogenous regulators of gene function. Aberrant regulation of microRNAs has been linked to various human diseases, most importantly cancer. Small molecule intervention of microRNA misregulation has the potential to provide new therapeutic approaches to such diseases. Here, we report the first small molecule inhibitors and activators of the liver-specific microRNA miR-122. This microRNA is the most abundant microRNA in the liver and is involved in hepatocellular carcinoma development and hepatitis C virus (HCV) infection. Our small molecule inhibitors reduce viral replication in liver cells and represent a new approach to the treatment of HCV infections. Moreover, small molecule activation of miR-122 in liver cancer cells selectively induced apoptosis through caspase activation, thus having implications in cancer chemotherapy. In addition to providing a new approach for the development of therapeutics, small molecule modifiers of miR-122 function are unique tools for exploring miR-122 biogenesis.