[3,2-b]indole oleanolic acid 28-O-[β-D-glucopyranosyl] ester | 1152414-31-7

• 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: [3,2-b]indole oleanolic acid 28-O-[β-D-glucopyranosyl] ester
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,14R,17R,18S,21S,26S)-2,13,13,17,18,24,24-heptamethyl-11-azaheptacyclo[15.12.0.02,14.04,12.05,10.018,27.021,26]nonacosa-4(12),5,7,9,27-pentaene-21-carboxylate
• CAS: 1152414-31-7
• 化学式: C₄₂H₅₉NO₇
• 分子量: 689.933
• InChiKey: NKNJPLHXTBYUIU-OCZDVFMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  50
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  132
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 [3,2-b]indole oleanolic acid 28-O-[β-D-glucopyranosyl] ester
  参考文献：
  名称：

  Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents

  摘要：

  Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including D-galactopyranosides, D-glucopyranosides, D-xylopyranoses, D-arabopyranoses and D-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K2CO3, Bu4NBr, CH2Cl2-H2O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxyvitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.019