(E)-4’-羟基-3,4,5-三甲氧基二苯乙烯 | 116519-00-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (E)-4’-羟基-3,4,5-三甲氧基二苯乙烯
• 中文别名: (E)-4'-羟基-3,4,5-三甲氧基二苯乙烯
• 英文名称: (E)-1-(4-hydroxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: (E)-4'-hydroxy-3,4,5-trimethoxystilbene；(E)-4-(3,4,5-trimethoxystyryl)phenol；3,4,5-trimethoxy-4'-hydroxystilbene；DMU-281；3',4',5'-trimethoxy-trans-stilben-4-ol；4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• CAS: 116519-00-7
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: PGNACKMMQGBVTN-SNAWJCMRSA-N

物化性质

• 熔点：
  191 °C(Solv: acetic acid, 80% (64-19-7))
• 沸点：
  440.2±40.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

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

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (E)-4’-羟基-3,4,5-三甲氧基二苯乙烯 在 三乙烯二胺 作用下， 以 十四烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-S-(4-(3,4,5-trimethoxystyryl)phenyl) dimethylcarbamothioate
  参考文献：
  名称：

  非凡的自由基清除剂：4-巯基苯甲酸酯

  摘要：

  在过去的十年中，与天然白藜芦醇白藜芦醇相比，开发出更多的活性抗氧化剂和癌症化学预防剂引起了极大的兴趣和兴奋。在这项工作中，基于以下启发而构建了八种白藜芦醇导向的4-巯基对苯二甲酸酯：硫酚应是比酚更强的自由基清除剂，并且它们与galvinoxyl（GO 。）和2,2-diphenyl-1-picrylhydrazyl（DPPH）的反应速率。）甲醇和乙酸乙酯中的自由基是通过在25°C下使用停止流UV / Vis光谱法测量的。动力学分析表明，4-巯基对苯二酚是非凡的自由基清除剂，用四苯乙烯基支架中的4-SH基团取代4-OH基团是提高白藜芦醇自由基清除活性的重要策略。令人惊讶的是，在甲醇中，一些4-巯基对苯二酚的活性是白藜芦醇的10 4倍，比已知的抗氧化剂（α-生育酚，抗坏血酸，槲皮素和trolox）的活性高数十倍至数百倍。基于酸化动力学分析讨论了详细的自由基清除机理。添加乙酸显着降低了GO 。和DPPH

  DOI：

  10.1002/chem.201103897
• 作为产物：
  描述：

  对羟基苯乙酸 在 喹啉 、 乙酸酐 、 铜 、 三乙胺 作用下， 生成 (E)-4’-羟基-3,4,5-三甲氧基二苯乙烯
  参考文献：
  名称：

  非凡的自由基清除剂：4-巯基苯甲酸酯

  摘要：

  在过去的十年中，与天然白藜芦醇白藜芦醇相比，开发出更多的活性抗氧化剂和癌症化学预防剂引起了极大的兴趣和兴奋。在这项工作中，基于以下启发而构建了八种白藜芦醇导向的4-巯基对苯二甲酸酯：硫酚应是比酚更强的自由基清除剂，并且它们与galvinoxyl（GO 。）和2,2-diphenyl-1-picrylhydrazyl（DPPH）的反应速率。）甲醇和乙酸乙酯中的自由基是通过在25°C下使用停止流UV / Vis光谱法测量的。动力学分析表明，4-巯基对苯二酚是非凡的自由基清除剂，用四苯乙烯基支架中的4-SH基团取代4-OH基团是提高白藜芦醇自由基清除活性的重要策略。令人惊讶的是，在甲醇中，一些4-巯基对苯二酚的活性是白藜芦醇的10 4倍，比已知的抗氧化剂（α-生育酚，抗坏血酸，槲皮素和trolox）的活性高数十倍至数百倍。基于酸化动力学分析讨论了详细的自由基清除机理。添加乙酸显着降低了GO 。和DPPH

  DOI：

  10.1002/chem.201103897

文献信息

• Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
  作者：Jian-Hua Liang、Liang Yang、Si Wu、Si-Si Liu、Mark Cushman、Jing Tian、Nuo-Min Li、Qing-Hu Yang、He-Ao Zhang、Yun-Jie Qiu、Lin Xiang、Cong-Xuan Ma、Xue-Meng Li、Hong Qing

  DOI：10.1016/j.ejmech.2017.05.025

  日期：2017.8

  discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。
• Synthesis of 3,4,5-Trimethoxy-4’-hydroxystilbene Derivatives and Crystal Structure of Ethyl {4-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]phenoxy}acetate
  作者：Li Baolin、Guo Jian、Zhang Xiquan、Lai Yitian、Hu Huaiming

  DOI：10.1515/znb-2007-0216

  日期：2007.2.1

  Several new 4’-O-substituted derivatives of 3,4,5-trimethoxy-4’-hydroxystilbene were synthesized and characterized by their IR and NMR spectra. The crystal structure of ethyl 4-[(E)-2-(3,4,5-trimethoxyphenyl) vinyl]phenoxy}acetate, one of these stilbene derivatives, has been solved by singlecrystal X-ray structure analysis. The results show that all carbon and oxygen atoms in the molecule are nearly coplanar except C(16), and molecules stack to a column arrangement owing to C-H···π interactions. Pairs of these columns are linked by other molecules, and these linker molecules themselves also produce a column along the other direction. A puckered cyclic tetramer R⁴ ₄ (46) is formed and the tetramer propagates itself via intermolecular hydrogen bonds and C-H···π interactions. In this way, molecules are interrelated and assembled to a two-dimensional layer structure.

  合成并表征了几种新的3,4,5-三甲氧基-4'-羟基亚苄基衍生物的4'-O取代衍生物，通过它们的红外和核磁共振光谱进行了表征。其中一种亚苄基衍生物乙酸乙酯4-[(E)-2-(3,4,5-三甲氧基苯基)乙烯基]苯氧基}的晶体结构已通过单晶X射线结构分析得到。结果表明，分子中的所有碳和氧原子都几乎共面，除了C(16)，由于C-H···π相互作用，分子堆积成柱状排列。这些柱状体成对连接，连接分子本身也沿另一方向形成柱状体。通过分子间氢键和C-H···π相互作用，形成呈褶曲状的环状四聚体R4 4 (46) ，四聚体沿着自身传播。通过这种方式，分子相互关联并组装成二维层状结构。
• CYP1-Activation and Anticancer Properties of Synthetic Methoxylated Resveratrol Analogues
  作者：Ketan C. Ruparelia、Keti Zeka、Kenneth J. M. Beresford、Nicola E. Wilsher、Gerry A. Potter、Vasilis P. Androutsopoulos、Federico Brucoli、Randolph R. J. Arroo

  DOI：10.3390/molecules29020423

  日期：——

  (Z)-stilbenoid combretastatin A4, have been considered as promising lead compounds for the development of anticancer drugs. The antitumour properties of stilbenoids are known to be modulated by cytochrome P450 enzymes CYP1A1 and CYP1B1, which contribute to extrahepatic phase I xenobiotic and drug metabolism. Thirty-four methyl ether analogues of resveratrol were synthesised, and their anticancer properties were

  天然存在的二苯乙烯类化合物，如 （E）-二苯乙烯类白藜芦醇和 （Z）-二苯乙烯类化合物 combretastatin A4，已被认为是开发抗癌药物的有前途的先导化合物。已知二苯乙烯类化合物的抗肿瘤特性受细胞色素 P450 酶 CYP1A1 和 CYP1B1 的调节，这有助于肝外 I 期外源性物质和药物代谢。合成白藜芦醇的 34 种甲基醚类似物，并在一组人乳腺细胞系上使用 MTT 细胞增殖测定评估其抗癌特性。表达 CYP1 的乳腺肿瘤细胞系比不具有 CYP1 活性的细胞系受白藜芦醇类似物的影响明显更强。使用分离的 CYP1 酶的代谢研究提供了进一步的证据，证明 （E）-二苯乙烯类化合物可以成为这些酶的底物。通过与合成标准品和 LC-MS 共洗脱研究进行比较来确认代谢产物的结构。最有前途的二苯乙烯类化合物是 （E）-4,3′，4′，5′-四甲氧基二苯乙烯 （DMU212）。该化合物本身显示出低至中度的细胞毒性，但在
• Formulation and process for modulating wound healing
  申请人：BioMendics, LLC

  公开号：US10426742B2

  公开（公告）日：2019-10-01

  Methods and compounds are disclosed for wound healing by modulating autophagy. A formulation for modulating autophagy comprises a first modulating compound (FAM) selected from compounds having the general structure (I): wherein: L represents a linker selected from —C≡C—, (a tolan), —CH═CH— (a stilbene, preferably trans); or —CRa═CRb— a stilbene derivative; where Ra and Rb are independently H or phenyl optionally substituted with —(R3)p or —(R4)q; R1 to R4 are independent substituents at any available position of the phenyl rings, preferably at 3, 3′, 4, 4′, and/or 5, 5′; and m, n, p, and q are independently 0, 1, 2, or 3 representing the number of substituents of the rings, respectively, but at least one of m or n must be ≥1. Each R1 to R2 is independently selected from substituents described herein, including but not limited to hydroxyl, alkoxy, halo, halomethyl and glycosides. The formulation may also include an auxiliary autophagy modulating compound (AAM) as described herein. The formulation may include a hydrogel formed by the compounds themselves or otherwise and may include salts and/or complexes.

  本发明公开了通过调节自噬促进伤口愈合的方法和化合物。用于调节自噬的制剂包括选自具有一般结构 (I) 的化合物的第一调节化合物 (FAM)： 其中L 代表选自-C≡C-（甲苯）、-CH═CH-（二苯乙烯，最好是反式）或-CRa═CRb-二苯乙烯衍生物的连接体；其中 Ra 和 Rb 独立地是 H 或任选被-(R3)p 或-(R4)q 取代的苯基； R1至R4是独立的取代基，位于苯基环的任何可用位置，优选位于3，3′、4，4′和/或5，5′；m、n、p和q分别独立地为0、1、2或3，代表环的取代基数目，但m或n中至少有一个必须≥1。每个 R1 至 R2 独立地选自本文所述的取代基，包括但不限于羟基、烷氧基、卤代、卤代甲基和苷。制剂还可包括本文所述的辅助自噬调节化合物（AAM）。制剂可包括由化合物本身或以其它方式形成的水凝胶，并可包括盐和/或复合物。
• Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Asit K. Chakraborti、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00112a036

  日期：1991.8

  An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in the five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Several cis-stilbenes, structurally similar to combretastatins, were highly cytotoxic in all five cell lines and these were also found to be active as inhibitors of tubulin polymerization. The most active compounds also inhibited the binding of colchicine to tubulin. The most potent of the new compounds, both as a tubulin polymerization inhibitor and as a cytotoxic agent, was (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene (5a). This substance was almost as potent as combretastatin A-4 (1a), the most active of the combretastatins, as a tubulin polymerization inhibitor. Compound 5a was found to be approximately 140 times more cytotoxic against HT-29 colon adenocarcinoma cells and about 10 times more cytotoxic against MCF-7 breast carcinoma cells than combretastatin A-4. However, 5a was found to be about 20 times less cytotoxic against A-549 lung carcinoma cells, 30 times less cytotoxic against SKMEL-5 melanoma cells, and 7 times less cytotoxic against MLM melanoma cells than combretastatin A-4. The relative potencies 5a > 8a > 6a for the cis, dihydro, and trans compounds, respectively, as inhibitors of tubulin polymerization are in agreement with the relative potencies previously observed for combretastatin A-4 (1a), dihydrocombretastatin A-4 (1c), and trans-combretastatin A-4 (1b). The relative potencies 5a > 8a > 6a were also reflected in the results of the cytotoxicity assays. Structure-activity relationships of this group of compounds are also discussed.