methyl 7,24-bis-O-(tert-butyldimethylsilyl)-27-deoxy-27-oxookadaate | 1644233-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 7,24-bis-O-(tert-butyldimethylsilyl)-27-deoxy-27-oxookadaate
• CAS: 1644233-51-1
• 化学式: C₅₇H₉₆O₁₃Si₂
• 分子量: 1045.55
• InChiKey: VPITYOXKZDSVMQ-ANWRYEBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.57
• 重原子数：
  72.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  146.67
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl 7,24-bis-O-(tert-butyldimethylsilyl)-27-deoxy-27-oxookadaate 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以92%的产率得到methyl 27-deoxy-27-oxookadaate
  参考文献：
  名称：

  Selective Elimination of Human Pluripotent Stem Cells by a Marine Natural Product Derivative

  摘要：

  One of the current obstacles to stem cell therapy is the tumorigenic potential of residual undifferentiated stem cells. The present study reports rediscovery of a synthetic derivative of okadaic acid, a marine polyether toxin, as a reagent that selectively induces the death of human pluripotent stem cells. Cell-based screening of 333 cytotoxic compounds identified methyl 27-deoxy-27-oxookadaate (molecule 1) as a substrate of two ATP-binding cassette (ABC) transporters, ABCB1 (MDR1) and ABCG2 (BCRP), whose expression is repressed in human embryonic stem cells and induced pluripotent stem cells. The results demonstrate that selective elimination of human pluripotent stern cells can be achieved by designing cytotoxic small molecules with appropriate ABC-transporter selectivity.

  DOI：

  10.1021/ja501795c
• 作为产物：
  描述：

  黑海棉酸钠盐 在 咪唑 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 9.33h， 生成 methyl 7,24-bis-O-(tert-butyldimethylsilyl)-27-deoxy-27-oxookadaate
  参考文献：
  名称：

  Selective Elimination of Human Pluripotent Stem Cells by a Marine Natural Product Derivative

  摘要：

  One of the current obstacles to stem cell therapy is the tumorigenic potential of residual undifferentiated stem cells. The present study reports rediscovery of a synthetic derivative of okadaic acid, a marine polyether toxin, as a reagent that selectively induces the death of human pluripotent stem cells. Cell-based screening of 333 cytotoxic compounds identified methyl 27-deoxy-27-oxookadaate (molecule 1) as a substrate of two ATP-binding cassette (ABC) transporters, ABCB1 (MDR1) and ABCG2 (BCRP), whose expression is repressed in human embryonic stem cells and induced pluripotent stem cells. The results demonstrate that selective elimination of human pluripotent stern cells can be achieved by designing cytotoxic small molecules with appropriate ABC-transporter selectivity.

  DOI：

  10.1021/ja501795c