tert-butyl (2-bromo-6-cyano-3-cyclohexyl-1H-indol-1-yl)acetate | 774214-11-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2-bromo-6-cyano-3-cyclohexyl-1H-indol-1-yl)acetate
• 英文别名: tert-butyl 2-(2-bromo-6-cyano-3-cyclohexylindol-1-yl)acetate
• CAS: 774214-11-8
• 化学式: C₂₁H₂₅BrN₂O₂
• 分子量: 417.346
• InChiKey: LERFXUWOHOKKPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-bromo-6-cyano-3-cyclohexyl-1H-indol-1-yl)acetate 在 bis-triphenylphosphine-palladium(II) chloride 盐酸羟胺 、 sodium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 [3-cyclohexyl-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-phenyl-1H-indol-1-yl]acetic acid
  参考文献：
  名称：

  Development of carboxylic acid replacements in indole-N-acetamide inhibitors of hepatitis C virus NS5B polymerase

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.06.093
• 作为产物：
  描述：

  2-溴-3-环己基-1H-吲哚-6-羧酸 在 吡啶 、 二碳酸二叔丁酯 、 sodium hydride 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 tert-butyl (2-bromo-6-cyano-3-cyclohexyl-1H-indol-1-yl)acetate
  参考文献：
  名称：

  Development of carboxylic acid replacements in indole-N-acetamide inhibitors of hepatitis C virus NS5B polymerase

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.06.093

文献信息

• Indole acetamides as inhibitors of the hepatitis c virus ns5b polymerase
  申请人：Avolio Salvatore

  公开号：US20070167447A1

  公开（公告）日：2007-07-19

  The present invention relates to indole and azaindole compounds of formula (I): wherein X 1 , X 2 , X 3 , X 4 , A 1 , Ar 1 , R 1 , R 2 and n are as defined herein, and pharmaceutically acceptable salts thereof, useful in the prevention and treatment of hepatitis C infections.

  本发明涉及式(I)的吲哚和氮杂吲哚化合物：其中X1，X2，X3，X4，A1，Ar1，R1，R2和n如本文所定义，并且其药学上可接受的盐，在预防和治疗丙型肝炎感染方面有用。