3-(2”,3”-di-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2’,3’-di-O-acetyl-α-L-rhamnopyranosyl)-emodin | 1242274-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-(2”,3”-di-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2’,3’-di-O-acetyl-α-L-rhamnopyranosyl)-emodin
• 英文别名: 3-(2',3'-di-O-acetyl-α-L-rhamnopyranosyl-(1->4)-2',3'-di-O-acetyl-α-L-rhamnopyranosyl)emodin；[(2S,3R,4R,5S,6S)-3-acetyloxy-2-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-(4,5-dihydroxy-7-methyl-9,10-dioxoanthracen-2-yl)oxy-2-methyloxan-3-yl]oxy-5-hydroxy-6-methyloxan-4-yl] acetate
• CAS: 1242274-71-0
• 化学式: C₃₅H₃₈O₁₇
• 分子量: 730.677
• InChiKey: ZVAOYJUIXGHAOO-JRTOFOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  237
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  3-(2',3'-di-O-acetyl-4'-O-levulinyl-α-L-rhamnopyranosyl-(1->4)-2',3'-di-O-acetyl-α-L-rhamnopyranosyl)emodin 在 乙酸肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以76.2%的产率得到3-(2”,3”-di-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2’,3’-di-O-acetyl-α-L-rhamnopyranosyl)-emodin
  参考文献：
  名称：

  Synthesis and biological evaluation of cytotoxic activity of novel anthracene l-rhamnopyranosides

  摘要：

  A series of anthracene L-rhamnopyranosides were designed and synthesized in a practical way and their cytotoxic activity was examined in vitro. Most compounds exhibited both potent cytotoxicity against several tumor cell lines and high DNA binding capacity. The preliminary results showed that subtle modifications of rhamnosyl moiety in anthracene rhamnosides with acetyl group had a selective toxicity for different tumor cells and the displacement of C-10 carbonyl group in emodin by acetylmethylene group was helpful to improve the inhibitory activity. Lipophilicity of the anthracene glycosides was not a crucial factor for cytotoxicity and most molecules with good cytotoxicity could inhibit the catalytic activity of Top2 alpha. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.064