(Z)-1-(4-acetoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene | 134029-61-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-1-(4-acetoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: (Z)-2-(4-acetoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene；(Z) 4-Acetoxy-3',5'-trimethoxystilbene；[4-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl] acetate
• CAS: 134029-61-1
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: SYAOAXJVQVJDPD-WAYWQWQTSA-N

物化性质

• 沸点：
  464.7±40.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-Acetoxy-α-(3,4,5-trimethoxyphenyl)zimtsaeure 在 喹啉 、 铜 作用下， 反应 2.0h， 以56%的产率得到(Z)-1-(4-acetoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene
  参考文献：
  名称：

  二苯乙烯衍生物对长白僵菌幼虫的合成及抗昆虫活性

  摘要：

  继续我们的寻找以天然产物为基础的化合物来控制长双歧杆菌幼虫的研究，首次合成了25种二苯乙烯类似物并评估了其对长双歧杆菌第三龄幼虫的昆虫拒食活性。在所有测试的化合物中，尤其是化合物3a，3c和6在AFC 50中表现出明显的拒食活性值分别为0.218、0.327和0.226 mg / mL。这些化合物的拒食活性范围不同，表明二苯乙烯骨架中化学结构的变化显着影响了此类化合物的活性谱，并且从中揭示了一些重要的SAR信息。此外，要了解25种合成的二苯乙烯类似物对拒食活性的结构要求，可采用比较分子场分析（CoMFA）模型，该模型得出的留一法（LOO）交叉验证相关系数（q 2）为0.533和非交叉验证的相关系数（r 2）的数值为0.929。总之，这些初步结果可能在指导潜在的新抗饲料开发中对斯蒂芬苯酯的进一步修饰中有用。

  DOI：

  10.1007/s00044-012-0212-x

文献信息

• Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Asit K. Chakraborti、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00112a036

  日期：1991.8

  An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in the five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Several cis-stilbenes, structurally similar to combretastatins, were highly cytotoxic in all five cell lines and these were also found to be active as inhibitors of tubulin polymerization. The most active compounds also inhibited the binding of colchicine to tubulin. The most potent of the new compounds, both as a tubulin polymerization inhibitor and as a cytotoxic agent, was (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene (5a). This substance was almost as potent as combretastatin A-4 (1a), the most active of the combretastatins, as a tubulin polymerization inhibitor. Compound 5a was found to be approximately 140 times more cytotoxic against HT-29 colon adenocarcinoma cells and about 10 times more cytotoxic against MCF-7 breast carcinoma cells than combretastatin A-4. However, 5a was found to be about 20 times less cytotoxic against A-549 lung carcinoma cells, 30 times less cytotoxic against SKMEL-5 melanoma cells, and 7 times less cytotoxic against MLM melanoma cells than combretastatin A-4. The relative potencies 5a > 8a > 6a for the cis, dihydro, and trans compounds, respectively, as inhibitors of tubulin polymerization are in agreement with the relative potencies previously observed for combretastatin A-4 (1a), dihydrocombretastatin A-4 (1c), and trans-combretastatin A-4 (1b). The relative potencies 5a > 8a > 6a were also reflected in the results of the cytotoxicity assays. Structure-activity relationships of this group of compounds are also discussed.
• STILBENE DERIVATIVES AS ANTICANCER AGENTS
  申请人：Research Corporation Technologies, Inc.

  公开号：EP0641301A1

  公开（公告）日：1995-03-08
• US5430062A
  申请人：——

  公开号：US5430062A

  公开（公告）日：1995-07-04
• [EN] STILBENE DERIVATIVES AS ANTICANCER AGENTS<br/>[FR] DERIVES DE STILBENE UTILISES COMME AGENTS ANTICANCEREUX
  申请人：——

  公开号：WO1993023357A1

  公开（公告）日：1993-11-25

  [EN] The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds amont those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.
  [FR] Dérivés de stilbène présentant une utilité comme agents anticancéreux. On peut utiliser lesdits composés afin de traiter des cancers susceptibles d'être traités avec ceux-ci, et dans un procédé de traitement desdits cancers. L'invention concerne également des compositions pharmaceutiques contenant lesdits composés. Les composés préférés parmi ceux décrits dans l'invention sont (Z)-1-(4-méthoxyphényl)-2-(3,4,5-triméthoxyphényl)éthène, (Z)-1-(4-méthylphényl)-2-(3,4,5-triméthoxyphényl)éthène, et l'hydrochlorate de 4-méthyl-3',4',5'-triméthoxybenzylaniline.
• Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae
  作者：Ying-Qian Liu、Xiao-Jing Li、Chun-Yan Zhao、Yan Lu、Wen-Qun Li、Zhen-Ling Liu、Gang Feng、Liu Yang

  DOI：10.1007/s00044-012-0212-x

  日期：2013.5

  25 stilbene analogs were synthesized and evaluated for insect antifeedant activity against third-instar larvae of B. longissima for the first time. Among all the tested compounds, especially compounds 3a, 3c, and 6 showed pronounced antifeedant activities with AFC50 values of 0.218, 0.327, and 0.226 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation

  继续我们的寻找以天然产物为基础的化合物来控制长双歧杆菌幼虫的研究，首次合成了25种二苯乙烯类似物并评估了其对长双歧杆菌第三龄幼虫的昆虫拒食活性。在所有测试的化合物中，尤其是化合物3a，3c和6在AFC 50中表现出明显的拒食活性值分别为0.218、0.327和0.226 mg / mL。这些化合物的拒食活性范围不同，表明二苯乙烯骨架中化学结构的变化显着影响了此类化合物的活性谱，并且从中揭示了一些重要的SAR信息。此外，要了解25种合成的二苯乙烯类似物对拒食活性的结构要求，可采用比较分子场分析（CoMFA）模型，该模型得出的留一法（LOO）交叉验证相关系数（q 2）为0.533和非交叉验证的相关系数（r 2）的数值为0.929。总之，这些初步结果可能在指导潜在的新抗饲料开发中对斯蒂芬苯酯的进一步修饰中有用。