3-环己基-1-二甲基氨基甲酰基甲基-2-苯基-1H-吲哚-6-羧酸甲酯 | 1027992-74-0

• 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: 3-环己基-1-二甲基氨基甲酰基甲基-2-苯基-1H-吲哚-6-羧酸甲酯
• 英文名称: Methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-phenylindole-6-carboxylate
• CAS: 1027992-74-0
• 化学式: C₂₆H₃₀N₂O₃
• 分子量: 418.536
• InChiKey: LKLWNHRMKKKVCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-环己基-1-二甲基氨基甲酰基甲基-2-苯基-1H-吲哚-6-羧酸甲酯 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-phenyl-1H-indole-6-carboxylic acid
  参考文献：
  名称：

  Development and Preliminary Optimization of Indole-N-Acetamide Inhibitors of Hepatitis C Virus NS5B Polymerase

  摘要：

  Allosteric inhibition of the hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase enzyme has recently emerged as a viable strategy toward blocking replication of viral RNA in cell-based systems. We report here a novel class of allosteric inhibitor of NS5B that shows potent affinity for the NS5B enzyme and effective inhibition of subgenomic HCV RNA replication in HUH-7 cells. Inhibitors from this class have promising characteristics for further development as anti-HCV agents.

  DOI：

  10.1021/jm049122i
• 作为产物：
  描述：

  3-环己烷吲哚-6-甲酸 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氯化碳 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 3-环己基-1-二甲基氨基甲酰基甲基-2-苯基-1H-吲哚-6-羧酸甲酯
  参考文献：
  名称：

  Development and Preliminary Optimization of Indole-N-Acetamide Inhibitors of Hepatitis C Virus NS5B Polymerase

  摘要：

  Allosteric inhibition of the hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase enzyme has recently emerged as a viable strategy toward blocking replication of viral RNA in cell-based systems. We report here a novel class of allosteric inhibitor of NS5B that shows potent affinity for the NS5B enzyme and effective inhibition of subgenomic HCV RNA replication in HUH-7 cells. Inhibitors from this class have promising characteristics for further development as anti-HCV agents.

  DOI：

  10.1021/jm049122i

文献信息

• Development of carboxylic acid replacements in indole-N-acetamide inhibitors of hepatitis C virus NS5B polymerase
  作者：Ian Stansfield、Marco Pompei、Immacolata Conte、Caterina Ercolani、Giovanni Migliaccio、Mark Jairaj、Claudio Giuliano、Michael Rowley、Frank Narjes

  DOI：10.1016/j.bmcl.2007.06.093

  日期：2007.9

  Allosteric inhibition of the hepatitis C virus (HCV) NS5B RNA-dependent RNA polyrnerase enzyme has recently emerged as a viable strategy toward blocking replication of viral RNA in cell-based systems. We report here 2 series of indole-N-acetamides, bearing physicochemically diverse carboxylic acid replacements, which show potent affinity for the NS5B enzyme with reduced potential for formation of glucuronide conjugates. Preliminary optimization of these series furnished compounds that are potent in the blockade of subgenomic HCV RNA replication in HUH-7 cells. (c) 2007 Elsevier Ltd. All rights reserved.
• Development and Preliminary Optimization of Indole-<i>N</i>-Acetamide Inhibitors of Hepatitis C Virus NS5B Polymerase
  作者：Steven Harper、Barbara Pacini、Salvatore Avolio、Marcello Di Filippo、Giovanni Migliaccio、Ralph Laufer、Raffaele De Francesco、Michael Rowley、Frank Narjes

  DOI：10.1021/jm049122i

  日期：2005.3.1

  Allosteric inhibition of the hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase enzyme has recently emerged as a viable strategy toward blocking replication of viral RNA in cell-based systems. We report here a novel class of allosteric inhibitor of NS5B that shows potent affinity for the NS5B enzyme and effective inhibition of subgenomic HCV RNA replication in HUH-7 cells. Inhibitors from this class have promising characteristics for further development as anti-HCV agents.