ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside) | 1390620-14-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside)
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl benzoate
• CAS: 1390620-14-0
• 化学式: C₆₂H₇₀O₁₀
• 分子量: 975.232
• InChiKey: UJLJABQGWNLXMT-KUASLESDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  72
• 可旋转键数：
  19
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside) 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到ergosterol-3-O-β-D-galactopyranoside
  参考文献：
  名称：

  Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicineCordyceps sinensis

  摘要：

  Ergosterol 3-O-beta-D-glucopyranoside (1a) and ergosterol 3-O-beta-D-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by H-1, C-13 NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.

  DOI：

  10.1080/10286020.2012.670220
• 作为产物：
  描述：

  苯甲酰氯 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside)
  参考文献：
  名称：

  Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicineCordyceps sinensis

  摘要：

  Ergosterol 3-O-beta-D-glucopyranoside (1a) and ergosterol 3-O-beta-D-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by H-1, C-13 NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.

  DOI：

  10.1080/10286020.2012.670220

文献信息

• Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicine<i>Cordyceps sinensis</i>
  作者：Zhen-Yuan Zhu、Qiang Yao、Yang Liu、Chuan-Ling Si、Jing Chen、Nian Liu、Hong-Yu Lian、Li-Na Ding、Yong-Min Zhang

  DOI：10.1080/10286020.2012.670220

  日期：2012.5

  Ergosterol 3-O-beta-D-glucopyranoside (1a) and ergosterol 3-O-beta-D-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by H-1, C-13 NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.