[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoate | 1372627-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoate
• CAS: 1372627-71-8
• 化学式: C₄₄H₅₄O₁₃
• 分子量: 790.905
• InChiKey: MQXZYUNEWMQRJD-MIRSFJNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  57
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  199
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 生成 [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoate
  参考文献：
  名称：

  Synthesis and biological evaluation of glyco-GA compounds as anticancer agents

  摘要：

  A series of novel glyco-gambogic acid (GA) compounds were synthesized and evaluated for their in vitro anti-proliferative activity against human hepatocellular carcinoma (HCC) cells. All compounds showed much better aqueous solubility (0.92-1.89 mg/mL) than GA (0.013 mg/mL), and displayed potent inhibition on HCC cells (1050: 0.21-12.23 mu mol/L) and little affects on non-tumor liver cells (IC50: 42.56-86.43 mu mol/L), suggesting that glyco-GA compounds selectively inhibi : HCC proliferation, and may be promising candidates for further intensive study. (C) 2012 Yi Hua Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.01.019