4-isovaleryl-9-butyryl-coniferol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-isovaleryl-9-butyryl-coniferol
• 英文别名: [4-[(E)-3-butanoyloxyprop-1-enyl]-2-methoxyphenyl] 3-methylbutanoate
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: JYMDRHXHPVGZKP-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  阿魏酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-isovaleryl-9-butyryl-coniferol
  参考文献：
  名称：

  Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

  摘要：

  A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2-12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses. A simple and efficient method was designed to prepare tripolinolate A and its 19 analogs including nine new chemical entities for bioactive assay. Tripolinolate A and its analog 4,9-diacetyl-coniferol were found to be the two most active compounds that significantly inhibited the proliferation of different cancer cell lines with IC50 values ranging from 0.36 to 12.9 mu M and induced apoptosis in tumor cells. Structure-activity relationship analysis suggested that the molecular size of acyl moieties at C-4 and C-9 position might have an effect on the activity of this type of coniferol derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.091

文献信息

• Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs
  作者：Lu Chen、Ying Liang、Tengfei Song、Komal Anjum、Wenling Wang、Siran Yu、Haocai Huang、Xiao-Yuan Lian、Zhizhen Zhang

  DOI：10.1016/j.bmcl.2015.04.091

  日期：2015.7

  A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2-12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses. A simple and efficient method was designed to prepare tripolinolate A and its 19 analogs including nine new chemical entities for bioactive assay. Tripolinolate A and its analog 4,9-diacetyl-coniferol were found to be the two most active compounds that significantly inhibited the proliferation of different cancer cell lines with IC50 values ranging from 0.36 to 12.9 mu M and induced apoptosis in tumor cells. Structure-activity relationship analysis suggested that the molecular size of acyl moieties at C-4 and C-9 position might have an effect on the activity of this type of coniferol derivatives. (C) 2015 Elsevier Ltd. All rights reserved.