(E)-2-hydroxy-3',4,5'-trimethoxystilbene | 397333-51-6

• 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-hydroxy-3',4,5'-trimethoxystilbene
• 英文别名: (E)-2-(3,5-dimethoxystyryl)-5-methoxyphenol；1,3-dimethoxy-5-[(E)-2-(2-hydroxy-4-methoxy-phenyl)-vinyl]-benzene；2-[2-(3,5-Dimethoxy-phenyl)-vinyl]-5-methoxy-phenol；2-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-5-methoxyphenol
• CAS: 397333-51-6
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: IBVZKTRMHHMIIS-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 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：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-hydroxy-3',4,5'-trimethoxystilbene 在 碘 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran
  参考文献：
  名称：

  重氮与醌和邻苯二酚硼酸酯的无过渡金属的C（sp2）-C（sp2）交叉偶联。

  摘要：

  无过渡金属的C（sp 2）-C（sp 2）开发了重氮醌与邻苯二酚硼酸酯的交叉偶联反应。通过该方案，可以在温和条件下以高收率或高收率获得各种联芳基和烯基苯酚。该反应具有多种功能，可用于药物和天然产物的衍生化。该方法的合成效用通过短取代多取代的三亚苯基和三种生物活性天然产物厚朴酚，苦味素M和呋喃呋喃A的合成得到证明。机理研究和密度泛函理论（DFT）计算表明，该反应涉及到硼酸酯由单重醌卡宾构成，然后通过逐步机理进行1,2-重排。

  DOI：

  10.1002/anie.202006542
• 作为产物：
  描述：

  2-氨基-5-甲氧基苯酚 在 盐酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 9.17h， 生成 (E)-2-hydroxy-3',4,5'-trimethoxystilbene
  参考文献：
  名称：

  重氮与醌和邻苯二酚硼酸酯的无过渡金属的C（sp2）-C（sp2）交叉偶联。

  摘要：

  无过渡金属的C（sp 2）-C（sp 2）开发了重氮醌与邻苯二酚硼酸酯的交叉偶联反应。通过该方案，可以在温和条件下以高收率或高收率获得各种联芳基和烯基苯酚。该反应具有多种功能，可用于药物和天然产物的衍生化。该方法的合成效用通过短取代多取代的三亚苯基和三种生物活性天然产物厚朴酚，苦味素M和呋喃呋喃A的合成得到证明。机理研究和密度泛函理论（DFT）计算表明，该反应涉及到硼酸酯由单重醌卡宾构成，然后通过逐步机理进行1,2-重排。

  DOI：

  10.1002/anie.202006542

文献信息

• Synthesis of (E)-2,3′,4,5′-tetramethoxy[2-11C]stilbene
  作者：Lutz Schweiger、Stuart Craib、Andrew Welch、Tim A. D. Smith

  DOI：10.1002/jlcr.1439

  日期：2007.11

  In this paper, we describe the radiosynthesis of the compound (E)-2,3′,4,5′-tetramethoxy[2-11C]stilbene, a potential, universal tumour positron emission tomography imaging agent. The production of (E)-2,3′,4,5′-tetramethoxy[2-11C]stilbene was carried out via 11C-methylation of (E)-2-(hydroxy)-3′,4,5′-trimethoxystilbene by using [11C]methyl trifluoromethanesulfonate ([11C]methyl triflate). (E)-2,3′,4,5′-tetramethoxy[2-11C]stilbene was obtained with a radiochemical purity greater than 95% in a 20 ± 2% decay-corrected radiochemical yield, based upon [11C]carbon dioxide. Synthesis, purification and formulation were completed on an average of 30 min following the end of bombardment (EOB). The specific radioactivity obtained was 1.9 ± 0.6 GBq/µmol at EOB. Copyright © 2007 John Wiley & Sons, Ltd.

  本文介绍了化合物(E)-2,3′,4,5′-四甲氧基[2-11C]二苯乙烯的放射合成，这是一种潜在的通用肿瘤正电子发射断层成像剂。(E)-2,3′,4,5′-四甲氧基[2-11C]二苯乙烯是通过使用[11C]三氟甲磺酸甲酯（[11C]三氟甲磺酸甲酯）对(E)-2-(羟基)-3′,4,5′-三甲氧基二苯乙烯进行 11C 甲基化制备的。根据[11C]二氧化碳的放射性化学收率，(E)-2,3′,4,5′-四甲氧基[2-11C]二苯乙烯的放射性化学纯度高于 95%，衰变校正放射性化学收率为 20 ± 2%。合成、纯化和配制平均在轰击结束（EOB）后 30 分钟内完成。在 EOB 时获得的比放射性为 1.9 ± 0.6 GBq/µmol。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.
• WO2009/1046
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and antiproliferative evaluation of 2-hydroxylated (E)-stilbenes
  作者：Yan Zhang、Mingyun Shen、Sunliang Cui、Tingjun Hou

  DOI：10.1016/j.bmcl.2014.10.009

  日期：2014.12

  A simple synthesis of 2-hydroxylated (E)-stilbenes was accomplished in good yields via oxidative coupling of 2-hydroxystyrenes and arylboronic acids, with Rh(III)-catalyst and Cu(OAc)(2) as oxidant. The antiproliferative evaluation of all the synthesized compounds were assessed on four different human cancer cell lines (Colo-205, MDA-468, HT29, and MGC80-3), and the results showed that several compounds exhibit strong antiproliferative activities (up to IC50 = 35 nM for MGC80-3). (C) 2014 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Discovery of Novel <i>trans</i>-Stilbene Analogues as Potent and Selective Human Cytochrome P450 1B1 Inhibitors
  作者：Sanghee Kim、Hyojin Ko、Jae Eun Park、Sungkyu Jung、Sang Kwang Lee、Young-Jin Chun

  DOI：10.1021/jm010298j

  日期：2002.1.1

  A series of trans-stilbene derivatives containing a 3,5-dimethoxyphenyl moiety were prepared through a new efficient solution phase synthetic pathway, and their inhibitory activities were evaluated on human cytochrome P450s (CYP) 1A1, 1A2, and 1B1 to find a potent and selective CYP1B1 inhibitor. We found that a substituent at the 2-position of the stilbene skeleton plays a very important role in discriminating between CYP1As and CYP1B1. Among the compounds tested, the most selective and potent CYP1B1 inhibitor was 2,3',4,5'-tetramethoxystilbene, Compound 7j, 2-[2-(3,5-dimethoxy-phenyl)vinyl]thiophene, showed greater inhibitory activities but had a lower selectivity toward all of the CYP1s tested.
• 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.