(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol | 133815-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
• 英文别名: 3,5-dimethoxy-4-β-D-glucopyranosyloxycinnamic alcohol；sinapyl alcohol 4-O-β-D-glucopyranoside；sinapyl-4-O-β-D-glucopyranoside；eleutheroside B；cis-syringin；syringin
• CAS: 133815-42-6
• 化学式: C₁₇H₂₄O₉
• 分子量: 372.372
• InChiKey: QJVXKWHHAMZTBY-GAGVYUBLSA-N

物化性质

• 沸点：
  642.6±55.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  乙酰溴葡糖 在 哌啶 、 lithium aluminium tetrahydride 、 sodium methylate 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 10.02h， 生成 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of cytotoxic cinnamic alcohol derivatives

  摘要：

  Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)-6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5 mu M, respectively. The structure-activity relationships of the derivatives are discussed.

  DOI：

  10.1080/14786410902830175

文献信息

• Synthesis and structure–activity relationship studies of cytotoxic cinnamic alcohol derivatives
  作者：Hong-Bin Zou、Liang Zhang、Lei-Xiang Yang、Liu-Qing Yang、Yu Zhao、Yong-Ping Yu、Joachim Stöckigt

  DOI：10.1080/14786410902830175

  日期：2011.2

  Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)-6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5 mu M, respectively. The structure-activity relationships of the derivatives are discussed.