tripolinolate A

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: tripolinolate A
• 英文别名: [4-[(E)-3-acetyloxyprop-1-enyl]-2-methoxyphenyl] (2S)-2-methylbutanoate
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: OGNZVIKZDOKDLK-SYTKJHMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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 tripolinolate A
  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

• Ruthenium-Catalyzed Cross-Metathesis of Allyl Acetate and Styrenes: A Practical Approach to the Synthesis of Tripolinolate A and Its Analogs
  作者：Yasuhiro Araki、Nikola Topolovčan、Martin Kotora

  DOI：10.1002/ejoc.201700132

  日期：2017.4.3

  structurally divergent styrenes were tolerated, and the resultant products were obtained in reasonable yields. The reported method was utilized in the synthesis of inhibitors of the proliferation of glioma and colorectal cancer cells, tripolinolate A and its diacetate analog.

  探索了 Ru 催化的乙酸烯丙酯和苯乙烯交叉复分解的范围。可以容忍各种电子和结构不同的苯乙烯，并以合理的产率获得所得产物。所报道的方法用于合成胶质瘤和结直肠癌细胞增殖抑制剂、三萜醇酯 A 及其二乙酸酯类似物。
• 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.