(Z)-1-(4-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)ethene | 134029-57-5

• 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-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: (Z)-2-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethene；4-nitro-3′,4′,5′-trimethoxy-(Z)-stilbene；(Z)-1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene；cis-3,4,5-trimethoxy-4'-nitrostilbene；1,2,3-trimethoxy-5-[(Z)-2-(4-nitrophenyl)ethenyl]benzene
• CAS: 134029-57-5
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: UDXWNMYENXAKPA-PLNGDYQASA-N

物化性质

• 沸点：
  445.3±40.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 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：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 四(三苯基膦)钯 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 22.58h， 生成 (Z)-1-(4-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)ethene
  参考文献：
  名称：

  A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors

  摘要：

  A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiproliferative activities in nanomolar concentrations. Among the compounds, 2a, 2b and 2e were the most active across three cancer cell lines. In addition, these compounds inhibited the polymerisation of tubulin in vitro more efficiently than CA-4. They caused cell cycle arrest in G(2)/M phase further confirming their ability to inhibit tubulin polymerisation.

  DOI：

  10.1016/j.bmc.2020.115684

文献信息

• Microwave-Assisted Solvent-Free Synthesis of (<i>E</i>)-Stilbenes
  作者：Liu-chang Wang、Jiang Li、Xi-quan Zhang、Hong-mei Gu、Bao-lin Li

  DOI：10.3184/174751912x13320888894748

  日期：2012.4

  An efficient synthesis of a series of stilbenes is reported using 4-nitrotoluene and substituted arylaldehydes as starting materials in the presence of Cs₂CO₃ and polyethylene glycol under solvent-free microwave irradiation. Compared with conventional method, this strategy exhibited higher stereoselectivity, shorter reaction times and has a lower environmental impact.

  报告以 4-硝基甲苯和取代的芳基醛为起始原料，在 Cs2CO3 和聚乙二醇存在下，在无溶剂微波辐照条件下高效合成了一系列二苯乙烯类化合物。与传统方法相比，该策略具有更高的立体选择性、更短的反应时间和更低的环境影响。
• Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae
  作者：Ying-Qian Liu、Xiao-Jing Li、Chun-Yan Zhao、Yan Lu、Wen-Qun Li、Zhen-Ling Liu、Gang Feng、Liu Yang

  DOI：10.1007/s00044-012-0212-x

  日期：2013.5

  25 stilbene analogs were synthesized and evaluated for insect antifeedant activity against third-instar larvae of B. longissima for the first time. Among all the tested compounds, especially compounds 3a, 3c, and 6 showed pronounced antifeedant activities with AFC50 values of 0.218, 0.327, and 0.226 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation

  继续我们的寻找以天然产物为基础的化合物来控制长双歧杆菌幼虫的研究，首次合成了25种二苯乙烯类似物并评估了其对长双歧杆菌第三龄幼虫的昆虫拒食活性。在所有测试的化合物中，尤其是化合物3a，3c和6在AFC 50中表现出明显的拒食活性值分别为0.218、0.327和0.226 mg / mL。这些化合物的拒食活性范围不同，表明二苯乙烯骨架中化学结构的变化显着影响了此类化合物的活性谱，并且从中揭示了一些重要的SAR信息。此外，要了解25种合成的二苯乙烯类似物对拒食活性的结构要求，可采用比较分子场分析（CoMFA）模型，该模型得出的留一法（LOO）交叉验证相关系数（q 2）为0.533和非交叉验证的相关系数（r 2）的数值为0.929。总之，这些初步结果可能在指导潜在的新抗饲料开发中对斯蒂芬苯酯的进一步修饰中有用。
• Inhibition of Restriction Enzymes EcoRI, BamHI and HindIII by Phenethylphenylphthalimides Derived from Thalidomide
  作者：Kazunori Motoshima、Minoru Ishikawa、Yuichi Hashimoto、Kazuyuki Sugita

  DOI：10.1248/cpb.59.880

  日期：——

  We discovered inhibitors of the restriction enzymes EcoRI, BamHI and HindIII by screening our library of compounds with a phenethylphenylphthalimide skeleton, based on α-glucosidase inhibitors and liver X receptor antagonists derived from thalidomide. Structural development afforded the potent restriction enzyme inhibitors 25 and 26.

  我们通过筛选具有苯乙基苯基邻苯二甲酰亚胺骨架的化合物库，发现了限制酶 EcoRI、BamHI 和 HindIII 的抑制剂，这些化合物的基础是来自沙利度胺的α-葡萄糖苷酶抑制剂和肝 X 受体拮抗剂。通过结构开发，获得了强效限制酶抑制剂 25 和 26。
• Indole-containing and combretastatin-related anti-mitotic and anti-tubulin polymerization agents
  申请人：Pinney G. Kevin

  公开号：US20050065217A1

  公开（公告）日：2005-03-24

  Trimethoxyphenyl substituted indole ligands have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin polymerization. Such compounds as well as related derivatives are excellent clinical candidates for the treatment of cancer in humans. In addition, certain of these ligands, as pro-drugs, may well prove to be tumor selective vascular targeting and destruction chemotherapeutic agents or to have anti-angiogenesis activity resulting in the selective prevention and/or destruction of tumor cell vasculature.

  已经发现了替甲氧苯基取代的吲哚配体，它们展示出令人印象深刻的细胞毒性以及抑制微管聚合的显着能力。这些化合物以及相关衍生物是治疗人类癌症的优秀临床候选药物。此外，其中某些配体作为前药，可能被证明是肿瘤选择性靶向血管破坏化学治疗药物，或具有抗血管生成活性，从而选择性地预防和/或破坏肿瘤细胞血管。
• 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.