1-piperidine-N-β-D-xylopyranoside | 764598-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-piperidine-N-β-D-xylopyranoside
• 英文别名: D-(1R)-1-piperidino-1,5-anhydro-xylitol；D-(1R)-1-Piperidino-1,5-anhydro-xylit；(2R,3R,4S,5R)-2-piperidin-1-yloxane-3,4,5-triol
• CAS: 764598-61-0
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: QWHOTNGCXYQCNU-UTINFBMNSA-N

物化性质

• 沸点：
  390.7±42.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  哌啶 、 D-吡喃木糖 以 甲醇 为溶剂， 反应 72.0h， 以4%的产率得到1-piperidine-N-β-D-xylopyranoside
  参考文献：
  名称：

  Novel d-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α

  摘要：

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.

  DOI：

  10.1021/jm8008713

文献信息

• Zeile; Kruckenberg, Chemische Berichte, 1942, vol. 75, p. 1127,1134
  作者：Zeile、Kruckenberg

  DOI：——

  日期：——
• Ida, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 501,502
  作者：Ida

  DOI：——

  日期：——