1-benzyl-3-(β-D-xylopyranosyl)-1H-indole | 1396259-95-2

• 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: 1-benzyl-3-(β-D-xylopyranosyl)-1H-indole
• 英文别名: (2S,3R,4S,5R)-2-(1-benzylindol-3-yl)oxane-3,4,5-triol
• CAS: 1396259-95-2
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: HMOYCJJKDQYDQA-WCIQWLHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzyl-3-[(2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)oxan-2-yl]indole 在 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 1-benzyl-3-(β-D-xylopyranosyl)-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors

  摘要：

  Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors are the current focus on the indication for the management of hyperglycemia in diabetes. Here, a novel series of C-linked indolylxyloside-based inhibitors of SGLT2 has been discovered. Structure-activity relationship studies revealed that substituents at the 7-position of the indole moiety and a p-cyclopropylphenyl group in the distal position were necessary for optimum inhibitory activity. The pharmacokinetic study demonstrates that the most potent compound 1i is metabolically stable with a low clearance in rats. In further efficacy study, 1i is found to significantly lower blood glucose levels of streptozotocin (STZ)-induced diabetic rats. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.053

文献信息

• NOVEL GLYCOSIDE COMPOUNDS
  申请人：National Health Research Institutes

  公开号：US20130157970A1

  公开（公告）日：2013-06-20

  Compounds of formula (I): wherein X, Y, and Z are defined herein. Also disclosed are pharmaceutical compositions and therapeutical methods related to these compounds.

  式（I）的化合物：其中X、Y和Z在此处定义。还披露了与这些化合物相关的药物组合物和治疗方法。
• [EN] NOVEL GLYCOSIDE COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS GLYCOSIDES
  申请人：NAT HEALTH RESEARCH INSTITUTES

  公开号：WO2013090550A1

  公开（公告）日：2013-06-20

  Compounds of formula (I) as shown in the disclosure, in which X, Y, and Z are defined herein. Also disclosed are pharmaceutical compositions and therapeutical methods related to these compounds.