(20β)-12β-O-(L-chloracetyl)dammarane-3β,20,25-triol | 1555375-12-6

• 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: (20β)-12β-O-(L-chloracetyl)dammarane-3β,20,25-triol
• 英文别名: (20R)-12β-O-(L-chloracetyl)dammarane-3β,20,25-triol；[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-12-yl] 2-chloroacetate
• CAS: 1555375-12-6
• 化学式: C₃₂H₅₅ClO₅
• 分子量: 555.239
• InChiKey: BNKPHPSLFQUVGS-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

• 作为产物：
  描述：

  25(R)-羟基原人参二醇 、 氯乙酰氯 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (20β)-12β-O-(L-chloracetyl)dammarane-3β,20,25-triol 、 3β,25-O-di-(L-chloracetyl)dammar-20(22)-ene-12β-ol 、 3β,12β-O-di-(L-chloracetyl)dammar-20(22)-ene-25-ol 、 (20R)-3β-O-(L-chloracetyl)dammarane-12β,20,25-triol 、 (20R)-3β,12β-O-di-(L-chloracetyl)dammarane-20,25-diol 、 (20R)-3β,25-O-di-(L-chloracetyl)dammarane-12β,20-diol 、 (20R)-20,25-O-di-(L-chloracetyl)dammarane-3β,12β-diol 、 3β-O-(L-chloracetyl)dammar-20(21)-ene-12β,25-diol 、 12β-O-(L-chloracetyl)dammar-20(21)-ene-3β,25-diol 、 25-O-(L-chloracetyl)dammar-20(21)-ene-3β,12β-diol 、 3β,12β-O-di-(L-chloracetyl)dammar-20(21)-ene-25-ol 、 12β-O-(L-chloracetyl)dammar-20(22)-ene-3β,25-diol
  参考文献：
  名称：

  Novel 25-hydroxyprotopanaxadiol derivatives incorporating chloroacetyl chloride and their anti-tumor evaluation

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.10.050

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.