(2S,3R,4S,5S,6R)-2-(3-(4-methoxyphenethyl)-6-methyl-1H-indol-4-yloxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol | 840538-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S,6R)-2-(3-(4-methoxyphenethyl)-6-methyl-1H-indol-4-yloxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[3-[2-(4-methoxyphenyl)ethyl]-6-methyl-1H-indol-4-yl]oxy]oxane-3,4,5-triol
• CAS: 840538-01-4
• 化学式: C₂₄H₂₉NO₇
• 分子量: 443.497
• InChiKey: VJAWUCGYIXJOSI-PFKOEMKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4-methoxybenzylidene)triphenylphosphorane 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 丙酮 为溶剂， -78.0~20.0 ℃ 、103.42 kPa 条件下， 反应 24.0h， 生成 (2S,3R,4S,5S,6R)-2-(3-(4-methoxyphenethyl)-6-methyl-1H-indol-4-yloxy)-6-(hydroxymethyl)-tetrahydro-2H-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

文献信息

• SUBSTITUTED INDOLE-O-GLUCOSIDES
  申请人：Beavers Mary Pat

  公开号：US20090105164A1

  公开（公告）日：2009-04-23

  Substituted indole-O-glucosides, compositions containing them, and methods of using them, for example for the treatment of diabetes and Syndrome X are disclosed.
• US7511022B2
  申请人：——

  公开号：US7511022B2

  公开（公告）日：2009-03-31
• US7820630B2
  申请人：——

  公开号：US7820630B2

  公开（公告）日：2010-10-26
• Heteroaryl-O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1
  作者：Xiaoyan Zhang、Maud Urbanski、Mona Patel、Roxanne E. Zeck、Geoffrey G. Cox、Haiyan Bian、Bruce R. Conway、Mary Pat Beavers、Philip J. Rybczynski、Keith T. Demarest

  DOI：10.1016/j.bmcl.2005.08.067

  日期：2005.12

  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.