1,5-anhydro-3-deoxy-D-glucitol 2,4,6-triphosphate | 1216904-97-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 1,5-anhydro-3-deoxy-D-glucitol 2,4,6-triphosphate
• 英文别名: [(2R,3S,5R)-3,5-diphosphonooxyoxan-2-yl]methyl dihydrogen phosphate
• CAS: 1216904-97-0
• 化学式: C₆H₁₅O₁₃P₃
• 分子量: 388.099
• InChiKey: CUWBCARTRRVMIX-NGJCXOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  210
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1,5-anhydro-3-deoxy-2,4,6-tris(dibenzylphosphoryl)-D-glucitol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 1,5-anhydro-3-deoxy-D-glucitol 2,4,6-triphosphate
  参考文献：
  名称：

  Development of carbohydrate-derived inhibitors of acid sphingomyelinase

  摘要：

  The acid sphingomyelinase is an emerging drug target, especially for inflammatory lung diseases. Presently, there are no directly-acting potent inhibitors available for cell-based studies. The potent inhibitor phosphatidylinositol-3,5-bisphosphate (PtdIns3,5P2) is not only unsuited for cell culture studies, but also does not provide hints for further structural improvements. In the SAR study described here, we replaced the inositolphosphate moiety by a carbohydrate derivative and the phosphatidic acid residue by an alkyl-sulfone ester. The resulting compound is more active than its parent compound and offers new means for further structural modification. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.030

文献信息

• Development of carbohydrate-derived inhibitors of acid sphingomyelinase
  作者：Anke G. Roth、S. Redmer、Christoph Arenz

  DOI：10.1016/j.bmc.2009.11.030

  日期：2010.1

  The acid sphingomyelinase is an emerging drug target, especially for inflammatory lung diseases. Presently, there are no directly-acting potent inhibitors available for cell-based studies. The potent inhibitor phosphatidylinositol-3,5-bisphosphate (PtdIns3,5P2) is not only unsuited for cell culture studies, but also does not provide hints for further structural improvements. In the SAR study described here, we replaced the inositolphosphate moiety by a carbohydrate derivative and the phosphatidic acid residue by an alkyl-sulfone ester. The resulting compound is more active than its parent compound and offers new means for further structural modification. (C) 2009 Elsevier Ltd. All rights reserved.