3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-4-hydroxy-indole-1-carboxylic acid diethylamide | 840537-84-0

• 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
• 英文名称: 3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-4-hydroxy-indole-1-carboxylic acid diethylamide
• 英文别名: 3-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]-N,N-diethyl-4-hydroxyindole-1-carboxamide
• CAS: 840537-84-0
• 化学式: C₂₃H₂₆N₂O₃
• 分子量: 378.471
• InChiKey: KFUJTZHVICUXDL-UHFFFAOYSA-N

物化性质

• 沸点：
  544.4±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-4-hydroxy-indole-1-carboxylic acid diethylamide 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 24.0h， 生成 (2S,3R,4S,5S,6R)-2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-1H-indol-4-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Heteroaryl-O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1

  摘要：

  A series of benzo-fused heteroaryl-O-glucosides was synthesized and evaluated in SGLT1 and 2 cell-based functional assays. Indole-O-glucoside 10a and benzimidazole-O-glucoside 18 exhibited potent in vitro SGLT2 inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.067
• 作为产物：
  描述：

  4-Benzyloxy-3-formyl-indole-1-carboxylic acid diethylamide 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、103.42 kPa 条件下， 生成 3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-4-hydroxy-indole-1-carboxylic acid diethylamide
  参考文献：
  名称：

  Heteroaryl-O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1

  摘要：

  A series of benzo-fused heteroaryl-O-glucosides was synthesized and evaluated in SGLT1 and 2 cell-based functional assays. Indole-O-glucoside 10a and benzimidazole-O-glucoside 18 exhibited potent in vitro SGLT2 inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.067

文献信息

• SUBSTITUTED INDOLE-O-GLUCOSIDES
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1680131A2

  公开（公告）日：2006-07-19
• EP1680131A4
  申请人：——

  公开号：EP1680131A4

  公开（公告）日：2009-05-27
• Substituted indole-O-glucosides
  申请人：Beavers Pat Mary

  公开号：US20050037981A1

  公开（公告）日：2005-02-17

  Substituted indole-O-glucosides, compositions containing them, and methods of using them, for example for the treatment of diabetes and Syndrome X are disclosed.
• Substituted indazole-O-glucosides
  申请人：Urbanski Maud

  公开号：US20060293251A1

  公开（公告）日：2006-12-28

  Substituted indole-O-glucosides, compositions containing them, and methods of using them, for example for the treatment of diabetes and Syndrome X are disclosed.
• US7129220B2
  申请人：——

  公开号：US7129220B2

  公开（公告）日：2006-10-31