(E)-1-(4-乙酰氧基苯基)-2-(2,3,4-三甲氧基苯基)乙烯 | 134029-69-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (E)-1-(4-乙酰氧基苯基)-2-(2,3,4-三甲氧基苯基)乙烯
• 英文名称: (E)-1-(4-acetoxyphenyl)-2-(2,3,4-trimethoxyphenyl)ethene
• 英文别名: (E)-4-(3,4,5-trimethoxystyryl)phenyl acetate；(E)-1-(4-Acetoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene；4-Acetoxy-3',5'-trimethoxystilbene；[4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl] acetate
• CAS: 134029-69-9
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: SYAOAXJVQVJDPD-AATRIKPKSA-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

• 作为反应物：
  描述：

  (E)-1-(4-乙酰氧基苯基)-2-(2,3,4-三甲氧基苯基)乙烯 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (E)-4’-羟基-3,4,5-三甲氧基二苯乙烯
  参考文献：
  名称：

  基于龙血中支架的成人海马神经发生有效刺激物的发现

  摘要：

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。

  DOI：

  10.1016/j.ejmech.2017.05.025
• 作为产物：
  描述：

  4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 40.5h， 生成 (E)-1-(4-乙酰氧基苯基)-2-(2,3,4-三甲氧基苯基)乙烯
  参考文献：
  名称：

  Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization

  摘要：

  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.

  DOI：

  10.1021/jm00112a036

文献信息

• Cytidine deaminase expression level in cancer as a new therapeutic target
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US11209421B2

  公开（公告）日：2021-12-28

  The present invention provides an in vitro method for selecting a patient affected with a tumor for a treatment with an antitumor compound, wherein the method comprises a step of measuring the expression level of CDA (Cytidine Deaminase) in a cancer sample from said patient. When the CDA expression level of a cancer sample is lower than the reference expression level, it is indicative that the patient is suitable for a treatment with an antitumor compound selected from the group consisting of the compounds of table 4, in particular aminoflavone. Alternatively, when the CDA expression level of a cancer sample is higher than the reference expression level, it is indicative that the patient is suitable for a treatment with an antitumor compound selected from the group consisting of the compounds of table 3, in particular dasatinib.

  本发明提供了一种选择肿瘤患者接受抗肿瘤化合物治疗的体外方法，其中该方法包括测量所述患者的癌症样本中CDA（胞苷脱氨酶）的表达水平的步骤。当癌症样本的CDA表达水平低于参考表达水平时，表明患者适合使用选自表4化合物组成的组的抗肿瘤化合物，特别是氨基黄酮进行治疗。或者，当癌症样本的CDA表达水平高于参考表达水平时，表明患者适合使用选自表3化合物组成的组的抗肿瘤化合物，特别是达沙替尼进行治疗。
• Heck arylation of styrenes with arenediazonium salts: short, efficient, and stereoselective synthesis of resveratrol, DMU-212, and analogues
  作者：Angélica Venturini Moro、Flávio Sega P. Cardoso、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2008.07.087

  日期：2008.9

  Short, efficient, and stereoselective synthesis of the trans-stilbenes resveratrol, DMU-212, and analogues of both compounds are described. The synthesis of these important anti-cancer agents feature the palladium catalyzed Heck-Matsuda arylation of styrenes with arenediazonium tetrafluoroborates. (C) 2008 Elsevier Ltd. All rights reserved.
• CYTIDINE DEAMINASE EXPRESSION LEVEL IN CANCER AS A NEW THERAPEUTIC TARGET
  申请人：Centre National de la Recherche Scientifique

  公开号：EP3436601A1

  公开（公告）日：2019-02-06
• 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.