28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside) | 66252-76-4

• 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-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside)
• 英文别名: 28-O-acetylbetulin-3-yl-α-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside；28-O-acetyl-betulin-3-yl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• CAS: 66252-76-4
• 化学式: C₄₆H₇₀O₁₂
• 分子量: 815.055
• InChiKey: QHDZKWWYQVOFJK-CCRRGBJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  58.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside) 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到B-10
  参考文献：
  名称：

  In vitro anticancer studies of α- and β-d-glucopyranose betulin anomers

  摘要：

  Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by H-1 and C-13 NMR spectroscopy as well as mass spectrometry. The crystal structure of 28-O-acetylbetulin-3-yl-beta-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside was determined. The compounds were tested against fifteen tumor cell lines of different histogenic origins. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside, exerted a dose dependent antiproliferative action towards the tumor cell lines. Treatment of HCT-116 cells for 24 h induced apoptosis, which was confirmed by the appearance of a typical ladder pattern in the DNA fragmentation assay and cell cycle analysis. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside seem to induce apoptosis by activation of different upstream caspases on colon cancer HCT-116 cell line. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2010.02.038
• 作为产物：
  描述：

  白桦脂醇 在 吡啶 、 4-二甲氨基吡啶 、 mercury(II) cyanide 作用下， 以 甲苯 为溶剂， 反应 50.0h， 生成 28-O-acetylbetulin 3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranoside)
  参考文献：
  名称：

  In vitro anticancer studies of α- and β-d-glucopyranose betulin anomers

  摘要：

  Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by H-1 and C-13 NMR spectroscopy as well as mass spectrometry. The crystal structure of 28-O-acetylbetulin-3-yl-beta-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside was determined. The compounds were tested against fifteen tumor cell lines of different histogenic origins. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside, exerted a dose dependent antiproliferative action towards the tumor cell lines. Treatment of HCT-116 cells for 24 h induced apoptosis, which was confirmed by the appearance of a typical ladder pattern in the DNA fragmentation assay and cell cycle analysis. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside seem to induce apoptosis by activation of different upstream caspases on colon cancer HCT-116 cell line. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2010.02.038

文献信息

• Glycosylation of betulin and its acetates in the presence of cadmium carbonate
  作者：L. �. Odinokova、G. I. Oshitok、V. A. Denisenko、V. F. Anufriev、A. M. Tolkach、N. I. Uvarova

  DOI：10.1007/bf00579477

  日期：——
• Glycosylation of triterpene alcohols of the lupane series
  作者：L. �. Odinokova、M. V. Denisenko、V. A. Denisenko、N. I. Uvarova

  DOI：10.1007/bf00596745

  日期：——
• Synthesis of triterpene and steroid glycosides
  作者：Nina I. Uvarova、Lyubov N. Atopkina、Georgi B. Elyakov

  DOI：10.1016/s0008-6215(00)85361-6

  日期：1980.8