diosgenyl 2,3,4,6-tetra-O-acetyl-α-L-arabinopyranosyl-(1->2)-4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside | 1019843-13-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: diosgenyl 2,3,4,6-tetra-O-acetyl-α-L-arabinopyranosyl-(1->2)-4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside
• CAS: 1019843-13-0
• 化学式: C₅₆H₇₈O₁₆
• 分子量: 1007.23
• InChiKey: IUZTUXGNELGREJ-CBOYPYDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  72.0
• 可旋转键数：
  9.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  179.04
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  diosgenyl 2,3,4,6-tetra-O-acetyl-α-L-arabinopyranosyl-(1->2)-4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside 在 溶剂黄146 、 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以47%的产率得到diosgenyl α-L-arabinopyranosyl-(1->2)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel spirostanic saponins and their cytotoxic activity

  摘要：

  This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.089
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-β-L-arabinopyranosyl trichloroacetimidate 、 diosgenyl 4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以56%的产率得到diosgenyl 2,3,4,6-tetra-O-acetyl-α-L-arabinopyranosyl-(1->2)-4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel spirostanic saponins and their cytotoxic activity

  摘要：

  This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.089