28-oxoallobetulin 3β-O-chacotrioside | 1159113-80-0

• 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: 28-oxoallobetulin 3β-O-chacotrioside
• 英文别名: (1R,4R,5R,8R,10S,13R,14R,17R,18R,19R)-10-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-23-one
• CAS: 1159113-80-0
• 化学式: C₄₈H₇₈O₁₆
• 分子量: 911.138
• InChiKey: JMIDUDJEXRNMCX-XMGSOJISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  64
• 可旋转键数：
  7
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  244
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 生成 28-oxoallobetulin 3β-O-chacotrioside
  参考文献：
  名称：

  Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products

  摘要：

  The concise synthesis, via a stepwise glycosylation approach, of lupeol, betulin and betulinic acid O-glycosides bearing a chacotriosyl moiety at the C-3 position is described. All neosaponins as well as their rearrangement products of the germanicane-type were evaluated in vitro for their anticancer and haemolytic activities. Although betulinic acid and betulin 3 beta-O-chacotriosides were neither cytotoxic nor haemolytic, their rearrangement products allobetulin and 28-oxoallobetulin 3 beta-O-chacotriosides (9 and 10) exhibited a cytotoxicity pro. le up to fourfold superior to betulinic acid against human breast (MCF7) and prostate (PC-3) adenocarcinomas cell lines (IC(50) = 10-18 mu M). One important result was that only chacotriosides featuring non-polar functions at the C-28 position (6, 9 and 10) exerted a haemolytic activity against red blood cells. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.076