(5R,8S,10S,13R,14S,17R)-4,4,10,13,14-Pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one | 861216-49-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (5R,8S,10S,13R,14S,17R)-4,4,10,13,14-Pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
• CAS: 861216-49-1
• 化学式: C₃₃H₅₂O₃
• 分子量: 496.774
• InChiKey: IZLRQCWPLKPYPT-DMUYISPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.28
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5R,8S,10S,13R,14S,17R)-4,4,10,13,14-Pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one 在 sodium hydroxide 、 氢溴酸 、 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 2-bromo-3-oxolanosta-1,9(11)-dien-24S,25-diol
  参考文献：
  名称：

  Synthetic lanostane-type triterpenoids as inhibitors of DNA topoisomerase II

  摘要：

  DNA topoisomerase (Topo) II is one of the target enzymes for chemotherapeutic drug development. Lanostane-type triterpenoids with various functional groups (-Cl, -Br, -OMe, -CHO, -CN, -COOH, and -COOMe) at C-2 were synthesized from 3-oxolanost-9(II)-en-24S,25-diol (9) isolated from Pinus luchuensis and their inhibitory effects on Topo II activity and cytotoxic activities against A549 cells were examined. All the derivatives showed Topo II inhibitory effects with IC50 values ranging from 1.86 to 149.97 mu M and cytotoxic activities with ED50 values ranging from 3.96 to 38.15 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.052
• 作为产物：
  描述：

  (5R,8S,10S,13R,14S,17R)-4,4,10,13,14-Pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 在 苯基氯化硒 、 双氧水 作用下， 以 乙酸乙酯 、 四氢呋喃 为溶剂， 以78%的产率得到(5R,8S,10S,13R,14S,17R)-4,4,10,13,14-Pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Synthetic lanostane-type triterpenoids as inhibitors of DNA topoisomerase II

  摘要：

  DNA topoisomerase (Topo) II is one of the target enzymes for chemotherapeutic drug development. Lanostane-type triterpenoids with various functional groups (-Cl, -Br, -OMe, -CHO, -CN, -COOH, and -COOMe) at C-2 were synthesized from 3-oxolanost-9(II)-en-24S,25-diol (9) isolated from Pinus luchuensis and their inhibitory effects on Topo II activity and cytotoxic activities against A549 cells were examined. All the derivatives showed Topo II inhibitory effects with IC50 values ranging from 1.86 to 149.97 mu M and cytotoxic activities with ED50 values ranging from 3.96 to 38.15 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.052