(E)-1-phenyl-2-(2,3,4-trimethoxyphenyl)ethene | 134029-70-2

• 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-phenyl-2-(2,3,4-trimethoxyphenyl)ethene
• 英文别名: 1,2,3-trimethoxy-4-[(E)-2-phenylvinyl]benzene；(E)-2,3,4-trimethoxystilbene；2,3,4-Trimethoxystilbene；1,2,3-trimethoxy-4-[(E)-2-phenylethenyl]benzene
• CAS: 134029-70-2
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: ZKXCILYDBWPWKZ-MDZDMXLPSA-N

物化性质

• 熔点：
  80-83 °C
• 沸点：
  395.5±37.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-2-(2,3,4-trimethoxyphenyl)ethene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 Trimethoxy bibenzyl
  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：

  反式-3-(2,3,4-三甲氧基苯基)-2-丙烯酸 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 lithium acetate 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 0.1h， 生成 (E)-1-phenyl-2-(2,3,4-trimethoxyphenyl)ethene
  参考文献：
  名称：

  Original one-pot microwave-promoted Hunsdiecker–Suzuki strategy: straightforward access to trans-1,2-diarylethenes from cinnamic acids

  摘要：

  An original strategy combining a Hunsdiecker-type bromodecarboxylation and a Suzuki cross-coupling reaction starting from various cinnamic acids has been developed in one-pot and under microwave heating to give trans-1,2-diaryiethenes in few minutes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.114

文献信息

• Substituted CIS- and trans-stilbenes as therapeutic agents
  申请人：Vander Jagt David L.

  公开号：US20070249647A1

  公开（公告）日：2007-10-25

  The present invention relates to method(s) of treating a subject afflicted with cancer or a precancerous condition, an inflammatory disease or condition, and/or stroke or other ischemic disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans-stilbene.

  本发明涉及治疗患有癌症或癌前病变、炎症性疾病或病情以及中风或其他缺血性疾病或病情的方法，该方法包括向需要的受试者或患者施用含有一定治疗有效量的取代的顺式或反式-芪的组合物。
• Mild and Efficient Aryl−Alkenyl Coupling via Pd(II) Catalysis in the Presence of Oxygen or Cu(II) Oxidants
  作者：Jay P. Parrish、Young Chun Jung、Seung Il Shin、Kyung Woon Jung

  DOI：10.1021/jo020159p

  日期：2002.10.1

  We report herein a mild and efficient method for carbon-carbon bond formation between aryl stannanes and olefins via Pd(II) catalysis in the presence of oxygen or Cu(II) oxidants as a reoxidant. The process allows reactions between various olefins and aryl stannanes of varying electron density. Coupling methods under these oxidation conditions are comparatively described, and the benefits and limitations are also discussed.
• Substituted <i>trans</i>-Stilbenes, Including Analogues of the Natural Product Resveratrol, Inhibit the Human Tumor Necrosis Factor Alpha-Induced Activation of Transcription Factor Nuclear Factor KappaB
  作者：Justin J. Heynekamp、Waylon M. Weber、Lucy A. Hunsaker、Amanda M. Gonzales、Robert A. Orlando、Lorraine M. Deck、David L. Vander Jagt

  DOI：10.1021/jm060630x

  日期：2006.11.30

  The transcription factor nuclear factor kappaB (NF-kappa B), which regulates expression of numerous antiinflammatory genes as well as genes that promote development of the prosurvival, antiapoptotic state is up-regulated in many cancer cells. The natural product resveratrol, a polyphenolic trans-stilbene, has numerous biological activities and is a known inhibitor of activation of NF-kappa B, which may account for some of its biological activities. Resveratrol exhibits activity against a wide variety of cancer cells and has demonstrated activity as a cancer chemopreventive against all stages, i.e., initiation, promotion, and progression. The biological activities of resveratrol are often ascribed to its antioxidant activity. Both antioxidant activity and biological activities of analogues of resveratrol depend upon the number and location of the hydroxy groups. In the present study, phenolic analogues of resveratrol and a series of substituted trans-stilbenes without hydroxy groups were compared with resveratrol for their abilities to inhibit the human tumor necrosis factor alpha-induced (TNF-alpha) activation of NF-kappa B, using the Panomics NF-kappa B stable reporter cell line 293/NF-kappa B-luc. A series of 75 compounds was screened to identify substituted trans-stilbenes that were more active than resveratrol. Dose-response studies of the most active compounds were carried out to obtain IC50 values. Numerous compounds were identified that were more active than resveratrol, including compounds that were devoid of hydroxy groups and were 100-fold more potent than resveratrol. The substituted trans-stilbenes that were potent inhibitors of the activation of NF-kappa B generally did not exhibit antioxidant activity. The results from screening were confirmed using BV-2 microglial cells where resveratrol and analogues were shown to inhibit LPS-induced COX-2 expression.
• 1,2,3-Trimethoxy-4-[(<i>E</i>)-2-phenylvinyl]benzene and (<i>E</i>,<i>E</i>)-1,4-bis(2,3,4-trimethoxyphenyl)buta-1,3-diene
  作者：Jana Sopková-de Oliveira Santos、Marc-Antoine Bazin、Jean-François Lohier、Laīla El Kihel、Sylvain Rault

  DOI：10.1107/s0108270109019702

  日期：2009.7.15

  The stilbene derivative 1,2,3-trimethoxy-4-[(E)-2-phenylvinyl]benzene, C17H18O3, (I), and its homocoupling co-product (E, E)-1,4-bis(2,3,4-trimethoxyphenyl) buta-1,3-diene, C22H26O6, (II), both have double bonds in trans conformations in their conjugated linkages. In the structure of stilbene (I), the aromatic rings deviate significantly from coplanarity, in contrast with coproduct (II), the core of which is rigorously planar. The deviation in stilbene (I) seems to be driven by intermolecular electrostatic interactions. Diene (II) sits on a crystallographic inversion centre, which bisects the conjugated linkage.
• STILBENE DERIVATIVES AS ANTICANCER AGENTS
  申请人：Research Corporation Technologies, Inc.

  公开号：EP0641301A1

  公开（公告）日：1995-03-08