(E)-1,2,3-trimethoxy-5-(3-methoxystyryl)benzene | 97399-88-7

• 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: (E)-1,2,3-trimethoxy-5-(3-methoxystyryl)benzene
• 英文别名: (E) 3,4,5-Tetramethoxystilbene；1,2,3-trimethoxy-5-[(E)-2-(3-methoxyphenyl)ethenyl]benzene
• CAS: 97399-88-7
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: HDVYOENGFYGXCE-CMDGGOBGSA-N

物化性质

• 沸点：
  435.6±40.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1,2,3-trimethoxy-5-(3-methoxystyryl)benzene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 dimethyl ether of aloifol I
  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
• 作为产物：
  描述：

  间甲基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 三(2-吡啶基甲基)胺 、 铜 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (E)-1,2,3-trimethoxy-5-(3-methoxystyryl)benzene
  参考文献：
  名称：

  铜/多胺促进的苄基宝石-二溴化物立体选择性还原偶联合成的E-二苯乙烯衍生物

  摘要：

  铜/多胺促进的苄基宝石二溴化物的立体选择性还原偶联反应在温和的条件下以高收率生成了E-二苯乙烯衍生物。它提供了使用便宜的试剂和不含烯基的起始原料并易于加工来合成对称和不对称E-苯乙烯衍生物的捷径。

  DOI：

  10.1016/j.tetlet.2017.05.072

文献信息

• A Concise Synthesis of Substituted Stilbenes and Styrenes from Propargylic Phosphonium Salts by a Cobalt-Catalyzed Diels−Alder/Wittig Olefination Reaction Sequence
  作者：Gerhard Hilt、Christoph Hengst

  DOI：10.1021/jo701406d

  日期：2007.9.1

  single synthetical step starting from three variable starting materials. The E/Z stereoselectivities of the products revealed that the dihydroaromatic phosphonium ylides behave as semistabilized ylides giving predominantly the E-configured products. The application of unsymmetrical 1,3-dienes as well as internal phosphonium functionalized alkynes is also described.

  炔丙基phospho盐和较长链炔烃官能化phospho盐与1,3-二烯的钴（I）催化Diels-Alder反应生成二氢芳族phospho盐中间体，可直接用于一锅Wittig型烯化反应中醛。随后的氧化导致在三种合成起始原料的单一合成步骤中，形成了三个新的碳-碳键，形成了苯乙烯和二苯乙烯型产品。产品的E / Z立体选择性表明，二氢芳族盐表现为半稳定化的ides化物，主要产生E配置的产品。还介绍了不对称1,3-二烯以及内部phospho官能化炔烃的应用。
• 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。
• Regioselective reductive demethoxylation of 3,4,5-trimethoxystilbenes
  作者：Ugo Azzena、Giovanna Dettori、Maria Vittoria Idini、Luisa Pisano、Grazia Sechi

  DOI：10.1016/j.tet.2003.08.009

  日期：2003.9

  Selective removal of the 4-methoxy group of 3,4,5-trimethoxystilbenes was performed under electron transfer conditions from Na metal in THF. Careful control of reaction conditions and quenching procedure allowed the synthesis of either (E)-3,5-dimethoxystilbenes or 3,5-dimethoxybibenzyls. (C) 2003 Elsevier Ltd. All rights reserved.
• COMBRETASTATIN DERIVATIVES WITH CYTOTOXIC ACTION
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP1646616A2

  公开（公告）日：2006-04-19
• 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