(20R)-3β-O-(L-chloracetyl)dammarane-12β,20,25-triol

• 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)-3β-O-(L-chloracetyl)dammarane-12β,20,25-triol
• 英文别名: [(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-12-hydroxy-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] 2-chloroacetate
• 化学式: C₃₂H₅₅ClO₅
• 分子量: 555.239
• InChiKey: ZLXZHBUQHPKAMH-QUMRLDBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-乙基哌嗪 、 (20R)-3β-O-(L-chloracetyl)dammarane-12β,20,25-triol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以53%的产率得到20(R)-25-hydroxydammarane-12β,20-diol-3β-yl [4-ethylpiperazin-1-yl]acetate
  参考文献：
  名称：

  Novel ginsenoside derivatives have shown their effects on PC-3 cells by inducing G1-phase arrest and reactive oxygen species-mediate cell apoptosis

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104864
• 作为产物：
  描述：

  25(R)-羟基原人参二醇 、 氯乙酸 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (20R)-3β-O-(L-chloracetyl)dammarane-12β,20,25-triol
  参考文献：
  名称：

  Novel ginsenoside derivatives have shown their effects on PC-3 cells by inducing G1-phase arrest and reactive oxygen species-mediate cell apoptosis

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104864

文献信息

• Novel 25-hydroxyprotopanaxadiol derivatives incorporating chloroacetyl chloride and their anti-tumor evaluation
  作者：Fan-Zhi Qu、Ya-Fei Liu、Jia-Qing Cao、Xu-De Wang、Xiao-Shu Zhang、Chen Zhao、Yu-Qing Zhao

  DOI：10.1016/j.bmcl.2014.10.050

  日期：2014.12

  In the current work, 12 novel 25-hydroxyprotopanaxadiol (25-OH-PPD) derivatives were synthesized by reacting with chloroacetyl chloride. And their in vitro antitumor activities were evaluated on six human tumor cell lines by MTT assay. The results demonstrated that, as compared with 25-OH-PPD, compounds 4, 6 and 7 exhibited higher cytotoxic activity on all tested cell lines. Of them, compound 4 showed strongly inhibition against MCF-7, HCT-116 and Lovo cells with IC50 values of 1.7, 1.6 and 2.1 mu M, respectively. The IC50 values of compound 6 against HCT-116 and 7 against MCF-7 were the lowest (1.2 and 1.6 mu M, respectively). It was also noted that compound 4 showed a 20- to 100-fold greater growth inhibition than ginsenoside-Rg(3) (an anti-cancer regular drug in China). In conclusion, the data revealed that compounds 4, 6 and 7 were potential candidates for anti-tumor treatment and may be useful for the development of novel antiproliferative agents. (C) 2014 Elsevier Ltd. All rights reserved.
• Novel ginsenoside derivatives have shown their effects on PC-3 cells by inducing G1-phase arrest and reactive oxygen species-mediate cell apoptosis
  作者：Shengnan Xiao、Xude Wang、Lei Xu、Dongyu Miao、Tao Li、Guangyue Su、Yuqing Zhao

  DOI：10.1016/j.bioorg.2021.104864

  日期：2021.7