(1S,3R,5R,9R,13R)-3-[4-(2,5-dihydroxyphenyl)butyl]-9-(hydroxymethyl)-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione | 1449216-04-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1S,3R,5R,9R,13R)-3-[4-(2,5-dihydroxyphenyl)butyl]-9-(hydroxymethyl)-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
• CAS: 1449216-04-9
• 化学式: C₂₇H₃₈O₉
• 分子量: 506.593
• InChiKey: KOXBRRKQUGLKSA-DAACTFMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.5h， 以100%的产率得到(1S,3R,5R,9R,13R)-3-[4-(2,5-dihydroxyphenyl)butyl]-9-(hydroxymethyl)-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
  参考文献：
  名称：

  Synthesis of Antineoplastic Analogs of Aplysiatoxin with Various Side Chain Structures

  摘要：

  We have recently developed a simplified analog of aplysiatoxin with anti-proliferative activity (1). To investigate the structure activity relationship of its side chain, an alternative synthetic route of 1 has been established. Via the key intermediate 6, p-hydroxyl or o,m-dihydroxyl derivatives (4 and 5) as well as 1 were synthesized and their biological activities were evaluated. Although the position of the hydroxyl group in the benzene ring did not change the affinity for protein kinase C isozymes or the ability to induce the Epstein-Barr virus early antigen, anti-proliferative activities against several human cancer cell lines of 1 were superior to those of 4.

  DOI：

  10.3987/com-12-s(n)8