(5R,7S,8R,9R,10S)-7-(3-(4-ethylbenzyl)-4-methylphenyl)-1,6-dioxaspiro[4.5]decane-8,9,10-triol | 1221496-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,7S,8R,9R,10S)-7-(3-(4-ethylbenzyl)-4-methylphenyl)-1,6-dioxaspiro[4.5]decane-8,9,10-triol
• 英文别名: (5R,7S,8R,9R,10S)-7-[3-[(4-ethylphenyl)methyl]-4-methylphenyl]-1,6-dioxaspiro[4.5]decane-8,9,10-triol
• CAS: 1221496-07-6
• 化学式: C₂₄H₃₀O₅
• 分子量: 398.499
• InChiKey: DDOXILQISMHBNE-URYYLNOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 甲酸 、 钯 作用下， 以 甲醇 为溶剂， 生成 (5R,7S,8R,9R,10S)-7-(3-(4-ethylbenzyl)-4-methylphenyl)-1,6-dioxaspiro[4.5]decane-8,9,10-triol
  参考文献：
  名称：

  C-Aryl glycoside inhibitors of SGLT2: Exploration of sugar modifications including C-5 spirocyclization

  摘要：

  Modifications to the sugar portion of C-aryl glycoside sodium glucose transporter 2 (SGLT2) inhibitors were explored, including systematic deletion and modification of each of the glycoside hydroxyl groups. Based on results showing activity to be quite tolerant of structural change at the C-5 position, a series of novel C-5 spiro analogues was prepared. Some of these analogues exhibit low nanomolar potency versus SGLT2 and promote urinary glucose excretion (UGE) in rats. However, due to sub-optimal pharmacokinetic parameters (in particular half-life), predicted human doses did not meet criteria for further advancement. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.075