(Z)-1-(4-bromophenyl)-2-(3,4,5-trimethoxyphenyl)ethene | 74809-51-1

• 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: (Z)-1-(4-bromophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: 3,4,5-trimethoxy-4'-bromo-cis-stilbene；3,5,4-trimethoxy-4'-bromo-cis-stilbene；5-(4-bromostyryl)-1,2,3-trimethoxybenzene；5-[(1Z)-2-(4-bromophenyl)ethenyl]-1,2,3-trimethoxybenzene；(Z)-2-(4'-bromophenyl)-1-(3,4,5-trimethoxyphenyl)ethene；(Z) 4-Bromo-3',5'-trimethoxystilbene；5-[(Z)-2-(4-bromophenyl)ethenyl]-1,2,3-trimethoxybenzene
• CAS: 74809-51-1
• 化学式: C₁₇H₁₇BrO₃
• 分子量: 349.224
• InChiKey: UBBBWYGKBDCYDY-PLNGDYQASA-N

物化性质

• 沸点：
  444.6±40.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-溴苯基)乙炔 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 [RuHCl(CO)(H₂IMes)(PCy₃)] 、 potassium trimethylsilonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (Z)-1-(4-bromophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
  参考文献：
  名称：

  含N-杂环碳烯的钌配合物催化HSiMe（OSiMe 3）2对末端炔烃的（Z）选择性氢化硅烷化

  摘要：

  所述N-杂环-碳烯-连接的钌络合物[RuHCl（CO）（H 2个IMES）（PCY 3）]显示出对（高催化活性Ž）与1,1,1,3-各种末端炔烃的氢化硅烷化-选择性， 5,5,5-七甲基三硅氧烷（HSiMe（OSiMe 3）2）。（Z）-烯基硅氧烷的立体保持衍生化允许合成生物活性化合物，例如有效的抗肿瘤剂和诱导型NO合酶的抑制剂。

  DOI：

  10.1021/acs.orglett.7b02477

文献信息

• One-Pot, Fluoride-Promoted Wittig Reaction
  作者：Tiziano Fumagalli、Guido Sello、Fulvia Orsini

  DOI：10.1080/00397910802654633

  日期：2009.5.22

  ethyl α-bromoacetate with aliphatic, aromatic, and heteroaromatic aldehydes in the presence of tri-n-butylphosphine and tetrabutylammonium fluoride produced α,β-unsaturated esters in good to excellent yields and E-stereoselectivity. Under the same conditions, reactions of ethyl α-bromopropionate, α-bromo acetonitrile, and α-bromoacetophenone with aliphatic and aromatic aldehydes in the presence of tri-n-butylphosphine

  摘要 开发了一种一锅法、氟化物促进的 Wittig 反应。在三正丁基膦和四丁基氟化铵的存在下，α-溴乙酸乙酯与脂肪族、芳香族和杂芳香族醛的反应产生了 α,β-不饱和酯，收率和 E-立体选择性都非常好。在相同条件下，α-溴丙酸乙酯、α-溴乙腈和 α-溴苯乙酮与脂肪族和芳香族醛在三正丁基膦和四丁基氟化铵的存在下反应，在良好的 E 中产生了预期的 α,β-不饱和衍生物-立体选择性。该协议扩展到半稳定叶立德并应用于一些考布他汀类似物的合成。
• Neuroprotective and Antineuroinflammatory Effects of Hydroxyl-Functionalized Stilbenes and 2-Arylbenzo[<i>b</i>]furans
  作者：Pei-Chun Chen、Wei-Jern Tsai、Yune-Fang Ueng、Tsai-Teng Tzeng、Hsiang-Ling Chen、Pei-Ru Zhu、Chia-Hsiang Huang、Young-Ji Shiao、Wen-Tai Li

  DOI：10.1021/acs.jmedchem.7b00376

  日期：2017.5.11

  The drugs currently used to treat Alzheimer’s disease (AD) are limited in the benefits they confer, and no medication has been clearly proven to cure or delay the progression of AD. Most candidate AD drugs are meant to reduce the production, aggregation, and toxicity of amyloid β (Aβ) or to promote Aβ clearance. Herein, we demonstrate the efficient synthesis of hydroxyl-functionalized stilbene and

  当前用于治疗阿尔茨海默氏病（AD）的药物在其带来的益处方面受到限制，并且没有任何药物被明确证明可以治愈或延缓AD的发展。大多数候选AD药物旨在减少淀粉样蛋白β（Aβ）的产生，聚集和毒性，或促进Aβ清除。在此，我们证明了羟基官能化的1,2-二苯乙烯和2-芳基苯并[ b ]呋喃衍生物的有效合成，并报道了这些酚类化合物在体外和动物模型中的神经保护作用和抗炎作用。结构-活性关系表明，2-芳基苯并[ b ]呋喃上的丙烯酸酯基团具有神经保护和抗炎作用。此外，化合物11和37这项研究基于对神经元细胞的神经保护作用，对神经胶质细胞的抗神经炎作用以及改善APP / PS1小鼠筑巢行为的能力，显示出作为疾病缓解性抗阿尔茨海默氏病药物的特殊开发潜力。这些结果表明2-芳基苯并[ b ]呋喃可能是治疗AD的候选化合物。
• 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
• 10.1021/acs.joc.4c00450
  作者：Grudzień, Krzysztof、Szeptuch, Zuzanna、Kubiszewski, Hubert、Chaładaj, Wojciech、Rybicka-Jasińska, Katarzyna

  DOI：10.1021/acs.joc.4c00450

  日期：——

  Herein, we describe a simple three-coordinate complex of Cu(I) with an NHC and 1,10-phenanthroline ligands as an effective photocatalyst for energy (e.g., olefin E/Z isomerization) and electron transfer (e.g., aryl halide dehalogenation) reactions under blue-light irradiation. This complex can be obtained in a one-pot procedure starting from commercially available reagents and green solvents (EtOH

  在此，我们描述了 Cu(I) 与 NHC 和 1,10-菲咯啉配体的简单三配位络合物作为能量（例如，烯烃E / Z异构化）和电子转移（例如，芳基卤脱卤）的有效光催化剂。蓝光照射下的反应。该复合物可以从市售试剂和绿色溶剂（EtOH、水）开始，通过一锅法获得。我们特此对其活动进行研究，并对其运作模式进行机械洞察。
• 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.