(1S,3R,5R,9R,13R)-9-(hydroxymethyl)-16,16-dimethyl-3-(4-phenylbutyl)-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione | 1255534-99-6

• 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)-9-(hydroxymethyl)-16,16-dimethyl-3-(4-phenylbutyl)-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
• CAS: 1255534-99-6
• 化学式: C₂₇H₃₈O₇
• 分子量: 474.595
• InChiKey: MCIAOHYVDXDCLF-HLGBLHBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 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：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 甲酸 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以25%的产率得到(1S,3R,5R,9R,13R)-9-(hydroxymethyl)-16,16-dimethyl-3-(4-phenylbutyl)-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
  参考文献：
  名称：

  Role of the phenolic hydroxyl group in the biological activities of simplified analogue of aplysiatoxin with antiproliferative activity

  摘要：

  The 18-deoxy derivative (3) of a simplified analogue (1) of aplysiatoxin with antiproliferative activity was synthesized to examine the role of the phenolic hydroxyl group at position 18 in the biological activities of 1. Compound 3 as well as 1 showed significant affinity for protein kinase C delta (PKC delta), and the antiproliferative activity of 3 was slightly higher than that of 1. However, the anti-tumor-promoting activity of 3 was less than that of 1 in vitro, suggesting that the phenolic hydroxyl group of 1 is necessary for the anti-tumor-promoting activity but not for the binding of PKCd and antiproliferative activity. Moreover, PKC isozyme selectivity of 3 was similar to that of 1, suggesting non-PKC receptors for these compounds to play some roles in the anti-tumor-promoting activity of 1. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.051