trans-2,3,4'-trimethoxystilbene | 59276-80-1

• 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: trans-2,3,4'-trimethoxystilbene
• 英文别名: (E)-2,3,4'-trimethoxystilbene；(E)-2,3,4'-Trimethoxystilben；2,3,4'-Trimethoxyl-trans-stilbene；1,2-dimethoxy-3-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
• CAS: 59276-80-1
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: PNQVRLHJWRKFCT-JXMROGBWSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  404.1±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：

  trans-2,3,4'-trimethoxystilbene 在 platinum(IV) oxide sodium hydroxide 、 氢气 、 三溴化硼 、 三氯化铁 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-Hydroxy-3,4'-dimethoxybibenzyl (Pellepiphyllin)
  参考文献：
  名称：

  Moosinhaltsstoffe-XVIII：合成叶绿素和lunularin

  摘要：

  通过Wittig型反应合成了2-羟基-3,4'-二甲氧基联苄基（=叶绿素）和3,4'-二羟基联苄基（lunulain）。2,3-二甲氧基苯甲醛与4-甲氧基苄基膦酸酯缩合为2,3,4'-三甲氧基sti，催化还原为2,3,4'-三甲氧基联苄，脱甲基为2,3,4'-三羟基联苄和部分甲基化产生蝶草素。通过使3-甲氧基苯甲醛与4-甲氧基苄基膦酸酯反应成3,4'-二甲氧基,，催化氢化成3,4'-二甲氧基联苄，并用三溴化硼脱甲基，来合成Lunularin。

  DOI：

  10.1016/0040-4020(76)80029-4
• 作为产物：
  描述：

  4-甲氧基苄醇 在 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 trans-2,3,4'-trimethoxystilbene
  参考文献：
  名称：

  Synthesis and Bioactivity of Resveratrol Analogues

  摘要：

  据报道，白藜芦醇能够增强SIRT1的表达，并通过刺激与哺乳动物SIRT1具有高度同源性的Sir2，显著模拟热量限制的效果。设计并合成了系列新型白藜芦醇衍生物，作为新型SIRT1激动剂的候选物质。通过核磁共振(1H NMR)光谱分析对合成的化合物进行了表征，并利用Bioscreen C MBR机器在100 μM/L浓度下检测了这些化合物对酵母亲本菌株BY4743的Sir2激活作用。与白藜芦醇相比，多个化合物表现出良好的Sir2激活活性。同时，还讨论了这些化合物的结构-活性关系与Sir2激活活性的相关性。

  DOI：

  10.14233/ajchem.2014.16226

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。
• 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.
• US8980954B2
  申请人：——

  公开号：US8980954B2

  公开（公告）日：2015-03-17