trans-3,5,2',3'-tetramethoxystilbene

• 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-3,5,2',3'-tetramethoxystilbene
• 英文别名: 1-[(E)-2-(2,3-dimethoxyphenyl)ethenyl]-3,5-dimethoxybenzene
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: ZBPWWMCBDYSYSI-CMDGGOBGSA-N

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

• 作为产物：
  描述：

  3,5-二甲氧基苄醇 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-3,5,2',3'-tetramethoxystilbene
  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

• Complete NMR data of methoxylated cis- and trans-stilbenes as well as 1,2-diphenylethanes
  作者：Geunhyeong Jo、Jiye Hyun、Doseok Hwang、Young Han Lee、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.2754

  日期：2011.6

  Resveratrol is a polyphenol isolated from many natural sources including grapes, mulberries, eucalyptus, spruce, lilies, and peanuts. The hydroxyl groups in polyphenols can be substituted with various functional groups, allowing production of multiple derivatives. NMR spectroscopy is used to identify new derivatives. Since the complete NMR data of the known derivatives can be useful for identification

  白藜芦醇是一种多酚，可从多种天然来源中分离出来，包括葡萄，桑berries，桉树，云杉，百合和花生。多酚中的羟基可以被各种官能团取代，从而可以生产多种衍生物。NMR光谱用于识别新的衍生物。由于已知衍生物的完整NMR数据可用于鉴定新分离的衍生物，因此，在这里，我们报道了14个甲氧基化的对苯二甲酸酯和4个1,2-二苯乙烷的合成及其NMR数据。
• Styrylheterocycles as a novel class inhibitor of cyclooxygenase-2-mediated prostaglandin E 2 production
  作者：Sang Kook Lee、Eun-Jung Park、Eunjung Lee、Hye-Young Min、Eun-Young Kim、Taeho Lee、Sanghee Kim

  DOI：10.1016/j.bmcl.2004.02.038

  日期：2004.5

  The inhibitory effects of a series of styrylheterocycles on the production of cyclooxygenase-2-mediated prostaglandin E, (PGE(2)) were evaluated in lipopolysaccharide-stimulated RAW264.7 murine macrophages. A new series of potential inhibitors, including 3-[2-(4-methoxy-phenyl)-vinyl]-thiophene, have been identified, thus providing novel chemical leads for the further development of potential inhibitors in this capacity. The suppression of COX-2 mRNA expression by the active styryl heterocycles, in part, was involved in the inhibitory activity against the overproduction of PGE(2).(C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and Bioactivity of Resveratrol Analogues
  作者：Junli Ao、Yuanmou Chen、Xiaoling Xu、Xu Zhang、Yue Yu、Peng Yu、Erbing Hua

  DOI：10.14233/ajchem.2014.16226

  日期：——

  It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.

  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。