9-oxo-9,10-dihydro-acridine-4-carboxylic acid (pyridin-2-ylmethyl)amide | 1085311-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-oxo-9,10-dihydro-acridine-4-carboxylic acid (pyridin-2-ylmethyl)amide
• 英文别名: 9-oxo-N-(2-pyridylmethyl)-10H-acridine-4-carboxamide；9-oxo-N-(pyridin-2-ylmethyl)-10H-acridine-4-carboxamide
• CAS: 1085311-51-8
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: ZXUBJWZWFKCCQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨甲基吡啶 、 4-羧基-9-茚酮 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以31%的产率得到9-oxo-9,10-dihydro-acridine-4-carboxylic acid (pyridin-2-ylmethyl)amide
  参考文献：
  名称：

  New acridone-4-carboxylic acid derivatives as potential inhibitors of Hepatitis C virus infection

  摘要：

  A new class of compounds - acridone derivatives - was tested using the direct fluorometric helicase activity assay to determine the inhibitory properties of the derivatives towards the NS3 helicase of Hepatitis C virus (HCV). The compounds were also tested as putative transcription inhibitors of in vitro transcription based on the DNA-dependent T7 RNA polymerase. Most of the acridone derivatives tested were transcription inhibitors; however, only four of them inhibited the NS3 helicase at low concentrations (IC50 from 3 mu M to 20 mu M) and were therefore selected for further studies on the mechanism of inhibition. The acridone derivatives probably act via intercalation into double- stranded nucleic acids but they may also interact directly with viral enzymes. Selected carboxamides were tested in the subgenomic HCV replicon system. Two of the compounds: N-(pyridin-4-yl)-amide and N-(pyridin-2-yl)-amide of acridone-4-carboxylic acid are efficient RNA replication inhibitors with selectivity indexes of 19.4 and 40.5, respectively, proving that the acridone derivatives may be regarded as potential antiviral agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.074

文献信息

• New acridone-4-carboxylic acid derivatives as potential inhibitors of Hepatitis C virus infection
  作者：Anna Stankiewicz-Drogon、Larisa G. Palchykovska、Valentina G. Kostina、Inna V. Alexeeva、Anatoly D. Shved、Anna M. Boguszewska-Chachulska

  DOI：10.1016/j.bmc.2008.08.074

  日期：2008.10

  A new class of compounds - acridone derivatives - was tested using the direct fluorometric helicase activity assay to determine the inhibitory properties of the derivatives towards the NS3 helicase of Hepatitis C virus (HCV). The compounds were also tested as putative transcription inhibitors of in vitro transcription based on the DNA-dependent T7 RNA polymerase. Most of the acridone derivatives tested were transcription inhibitors; however, only four of them inhibited the NS3 helicase at low concentrations (IC50 from 3 mu M to 20 mu M) and were therefore selected for further studies on the mechanism of inhibition. The acridone derivatives probably act via intercalation into double- stranded nucleic acids but they may also interact directly with viral enzymes. Selected carboxamides were tested in the subgenomic HCV replicon system. Two of the compounds: N-(pyridin-4-yl)-amide and N-(pyridin-2-yl)-amide of acridone-4-carboxylic acid are efficient RNA replication inhibitors with selectivity indexes of 19.4 and 40.5, respectively, proving that the acridone derivatives may be regarded as potential antiviral agents. (C) 2008 Elsevier Ltd. All rights reserved.