(2R,3S,4S,5R,6S)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-2-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-3,4-diol | 1221496-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6S)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-2-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-3,4-diol
• 英文别名: (2R,3S,4S,5R,6S)-6-[4-chloro-3-[(4-methoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)-5-methoxyoxane-3,4-diol
• CAS: 1221496-02-1
• 化学式: C₂₁H₂₅ClO₆
• 分子量: 408.879
• InChiKey: XOOXXVXSVGKKRY-CRSSMBPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 水 、 三氟乙酸 作用下， 反应 1.0h， 生成 (2R,3S,4S,5R,6S)-6-(4-chloro-3-(4-methoxybenzyl)phenyl)-2-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-3,4-diol
  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