1-[(E)-2-(4-methoxyphenyl)ethenyl]-2,5-dimethoxybenzene | 361375-77-1

• 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: 1-[(E)-2-(4-methoxyphenyl)ethenyl]-2,5-dimethoxybenzene
• 英文别名: (E)-2',4,5'-trimethoxystilbene；(E)-2,4',5-trimethoxystilbene；(E)-2,5,4'-trimethoxystilbene；(E)2',4,5'-Trimethoxystilbene；1,4-dimethoxy-2-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
• CAS: 361375-77-1
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: DLCNDQOPSZAQAT-QPJJXVBHSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  421.8±35.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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

• 作为反应物：
  描述：

  1-[(E)-2-(4-methoxyphenyl)ethenyl]-2,5-dimethoxybenzene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以85%的产率得到2,5,4'-Trimethoxybibenzyl
  参考文献：
  名称：

  Activity of a hydroxybibenzyl bryophyte constituent against Leishmania spp. and Trypanosoma cruzi: In silico, in vitro and in vivo activity studies

  摘要：

  The synthesis and potent antiprotozoal activity of 14-hydroxylunularin, a natural hydroxybibenzyl bryophyte constituent is reported. 14-Hydroxylunularin was highly active in vitro assays against culture and intracellular forms of Leishmania spp. and Trypanosoma. cruzi, in absence of cytotoxicity against mammalian cells. Preliminary structure-activity relationship studies showed that the reported bioactivity depends on hybridization at the carbon-carbon bridge, position and number of free hydroxy group on the aromatic rings. The reported results were also in agreement with the in silico prediction using Non-Stochastic Quadratic Fingerprints-based algorithms. The same compound also showed antiprotozoal activity in Leishmania spp. infected mice by oral and subcutaneous administration routes, with an optimal treatment of a daily subcutaneous administration of 10 mg/kg of body weight for 15 days. This study suggested that 14-hydroxylunularin may be chosen as a new candidate in the development of leishmanicidal therapy. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.007
• 作为产物：
  描述：

  4-甲氧基苯乙烯 、 2-碘-1,4-二甲氧基苯 在 三乙醇胺 、 palladium diacetate 作用下， 反应 24.0h， 以56%的产率得到1-[(E)-2-(4-methoxyphenyl)ethenyl]-2,5-dimethoxybenzene
  参考文献：
  名称：

  Synthesis and biological evaluation of novel (E) stilbene-based antitumor agents

  摘要：

  Several new (E) stilbenes were synthesized by a combination of a Wittig olefination followed by Mizoroki-Heck coupling reactions. These compounds were screened for antitumor activity in a panel of 8 human cancer cell lines by a colorimetric SRB assay. Several of these compounds exhibit strong cytotoxicity. The most active compound of this series showed an average IC50 value of 0.03 mu mol; it acts by apoptosis as shown by a dye-exclusion test, an extra acridine orange/ethidium bromide staining and DNA-laddering experiments. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.015

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。
• A facile and rapid access to resveratrol derivatives and their radioprotective activity
  作者：Saori Uzura、Emiko Sekine-Suzuki、Ikuo Nakanishi、Motohiro Sonoda、Shinji Tanimori

  DOI：10.1016/j.bmcl.2016.07.018

  日期：2016.8

  A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes

  基于芳基硼酸与苯乙烯的钯催化氧化Heck反应，然后以中等至良好的产率脱甲基，可以轻松快速地获得白藜芦醇衍生物。易于合成一系列具有各种官能团的白藜芦醇衍生物。还已经使用大鼠胸腺细胞评估了合成化合物的放射防护活性。结果表明，一些白藜芦醇衍生物有效地保护了胸腺细胞免受辐射诱导的细胞凋亡。
• 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.