(1S,3R,5R,9R,13R)-9-((R)-1-(benzyloxy)ethyl)-3-(4-(3-(benzyloxy)phenyl)butyl)-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione | 1449419-42-4

• 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-((R)-1-(benzyloxy)ethyl)-3-(4-(3-(benzyloxy)phenyl)butyl)-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
• CAS: 1449419-42-4
• 化学式: C₄₂H₅₂O₈
• 分子量: 684.87
• InChiKey: PDLQJRQPMYUMQI-MLRMZRIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.28
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,5R,9R,13R)-9-((R)-1-(benzyloxy)ethyl)-3-(4-(3-(benzyloxy)phenyl)butyl)-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到(1S,3R,5R,9R,13R)-9-[(1R)-1-hydroxyethyl]-3-[4-(3-hydroxyphenyl)butyl]-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
  参考文献：
  名称：

  Structure–activity studies at position 27 of aplog-1, a simplified analog of debromoaplysiatoxin with anti-proliferative activity

  摘要：

  Aplog-1, a simplified analog of debromoaplysiatoxin with anti-proliferative activity, bound to and activated protein kinase delta (PKC delta), that is involved in tumor suppression and apoptosis. To examine the contribution of PKC delta to the anti-proliferative activity of aplog-1, we synthesized 27-methyl and 27-methoxy derivatives that differed in the ability to activate PKC delta. Activators of PKC delta like aplog-1 and 27-(R)-Me-aplog-1 strongly inhibited the growth of several cancer cell lines. On the other hand, 27-(S)-Me-aplog-1 and 27-O-Me-aplog-1 without the ability to activate PKC delta, exhibited only weak growth inhibitory activity against these cell lines. These results suggest indirectly that the activation of PKC delta might be involved in the anti-proliferative activity of aplog-1 against aplog-sensitive cancer cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.008
• 作为产物：
  描述：

  (3R,4R)-4-(benzyloxy)-3-((4-methoxybenzyl)oxy)pentanoic acid 在 咪唑 、 potassium permanganate 、 sodium periodate 、 2,4,6-三氯苯甲酰氯 、 氟化氢吡啶 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 38.13h， 生成 (1S,3R,5R,9R,13R)-9-((R)-1-(benzyloxy)ethyl)-3-(4-(3-(benzyloxy)phenyl)butyl)-16,16-dimethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
  参考文献：
  名称：

  Structure–activity studies at position 27 of aplog-1, a simplified analog of debromoaplysiatoxin with anti-proliferative activity

  摘要：

  Aplog-1, a simplified analog of debromoaplysiatoxin with anti-proliferative activity, bound to and activated protein kinase delta (PKC delta), that is involved in tumor suppression and apoptosis. To examine the contribution of PKC delta to the anti-proliferative activity of aplog-1, we synthesized 27-methyl and 27-methoxy derivatives that differed in the ability to activate PKC delta. Activators of PKC delta like aplog-1 and 27-(R)-Me-aplog-1 strongly inhibited the growth of several cancer cell lines. On the other hand, 27-(S)-Me-aplog-1 and 27-O-Me-aplog-1 without the ability to activate PKC delta, exhibited only weak growth inhibitory activity against these cell lines. These results suggest indirectly that the activation of PKC delta might be involved in the anti-proliferative activity of aplog-1 against aplog-sensitive cancer cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.008