(E)-2,4',6-trimethoxystilbene

• 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)-2,4',6-trimethoxystilbene
• 英文别名: 9E-2,4',6-trimethoxystilbene；1,3-dimethoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: AURNOCORGLXLBS-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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

• 作为产物：
  描述：

  4-甲氧基苄醇 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.0h， 生成 (E)-2,4',6-trimethoxystilbene
  参考文献：
  名称：

  Quinone reductase induction activity of methoxylated analogues of resveratrol

  摘要：

  Agents that induce the activity of phase II enzymes play an important role in intervening with the carcinogenic process at the initiation stage. Resveratrol is well known for its chemopreventive activity against major stages of carcinogenesis. In this study, several methoxylated analogues of resveratrol were synthesized and evaluated for their ability to induce the activity of the phase H enzyme quinone reductase (QR). Methoxy groups serve to increase lipophilicity and improve metabolic stability. Compared to resveratrol, analogues with ortho-metboxy substituents were found to be more potent inducers of QR and to exert their activity in a qualitatively different manner. The greater induction activities associated with these stilbenoids serve as a useful starting point for the design of improved chemopreventive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.12.012

文献信息

• Substrate-Dependent Mechanistic Divergence in Decarboxylative Heck Reaction at Room Temperature
  作者：Asik Hossian、Samir Kumar Bhunia、Ranjan Jana

  DOI：10.1021/acs.joc.6b00100

  日期：2016.3.18

  We report herein a Pd(II)-catalyzed Heck-type coupling between arene carboxylic acids and alkenes at room temperature. Mechanistically, the reaction proceeds in two distinct pathways where electron-rich substrates undergo a palladium(II)-catalyzed decarboxylation and electron-deficient substrates proceed through silver(I)-assisted decarboxylation. Dimethyl sulfoxide (DMSO) or sulfide ligands have positive

  我们在这里报道了在室温下芳烃羧酸和烯烃之间的Pd（II）催化的Heck型偶联。从机理上讲，反应以两种不同的途径进行，富电子的底物经历钯（II）催化的脱羧反应，缺电子的底物通过银（I）辅助的脱羧反应进行。二甲基亚砜（DMSO）或硫化物配体在反应结果中分别具有正作用和负作用。结合本方案用于在温和的反应条件下进行肽修饰。
• 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。
• 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.
• SUBSTITUTED CIS- AND TRANS-STILBENES AS THERAPEUTIC AGENTS
  申请人：STC. UNM

  公开号：US20130178536A1

  公开（公告）日：2013-07-11

  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. A method of treating or reducing the likelihood of Alzheimer's disease in a patient is an additional embodiment of the present invention.
• THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS
  申请人：STC. UNM

  公开号：US20160287531A1

  公开（公告）日：2016-10-06

  The present invention relates to method(s) of treating a subject afflicted with a skin 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 or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.