(20R)-25-methoxy-dammarane-20-ol-3β,12β-diyl-3’,5’-dimethylbenzoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (20R)-25-methoxy-dammarane-20-ol-3β,12β-diyl-3’,5’-dimethylbenzoate
• 英文别名: [(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-(3,5-dimethylbenzoyl)oxy-17-[(2R)-2-hydroxy-6-methoxy-6-methylheptan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3,5-dimethylbenzoate
• 化学式: C₄₉H₇₂O₆
• 分子量: 757.107
• InChiKey: DUIYLICYICDRIB-AMYFYTCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  55
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二甲基苯甲酸 、 (20R)-25-methoxydammarane-3β,12β,20-triol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以16%的产率得到(20R)-25-methoxy-dammarane-20-ol-3β,12β-diyl-3’,5’-dimethylbenzoate
  参考文献：
  名称：

  Semi-synthesis and anti-tumor activity of novel 25-OCH3-PPD derivatives incorporating aromatic moiety

  摘要：

  Previously we have reported that 25-OCH3-PPD could suppress the reproduction of cancer cells and cause apoptosis without obvious toxicity. Herein, we aimed to enhance its bioactivity by introducing aromatic groups to its dammarane-type skeleton. These synthesized derivatives were tested for their inhibitory activities against five cancer cell lines. Of them, compounds 3a, 14a and 18a had the strongest antiproliferative activities against tumor cells (IC50 < 15 mu M, 5-fold to 10-fold increases than 25-OCH3-PPD). Especially compound 14a displayed the most potent activity against DU145, MCF-7 and HepG2 cells (IC50 = 6.7 +/- 0.8, 4.3 +/- 0.8 and 5.8 +/- 0.6 mu M, respectively). Structure-activity relationships demonstrated that having aromatic ester at the C3 position could improve the bioactivity. The data provided new insights into exploring novel antiproliferative lead compounds.

  DOI：

  10.1016/j.bmcl.2018.12.003

文献信息

• Semi-synthesis and anti-tumor activity of novel 25-OCH3-PPD derivatives incorporating aromatic moiety
  作者：Fan-Zhi Qu、Sheng-Nan Xiao、Xu-De Wang、Yan Zhang、Guang-Yue Su、Yu-Qing Zhao

  DOI：10.1016/j.bmcl.2018.12.003

  日期：2019.1

  Previously we have reported that 25-OCH3-PPD could suppress the reproduction of cancer cells and cause apoptosis without obvious toxicity. Herein, we aimed to enhance its bioactivity by introducing aromatic groups to its dammarane-type skeleton. These synthesized derivatives were tested for their inhibitory activities against five cancer cell lines. Of them, compounds 3a, 14a and 18a had the strongest antiproliferative activities against tumor cells (IC50 < 15 mu M, 5-fold to 10-fold increases than 25-OCH3-PPD). Especially compound 14a displayed the most potent activity against DU145, MCF-7 and HepG2 cells (IC50 = 6.7 +/- 0.8, 4.3 +/- 0.8 and 5.8 +/- 0.6 mu M, respectively). Structure-activity relationships demonstrated that having aromatic ester at the C3 position could improve the bioactivity. The data provided new insights into exploring novel antiproliferative lead compounds.