1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene | 7560-41-0

• 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: 1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene
• 英文别名: 4'-Nitro-3,4,5-trimethoxy-stilben；1,2,3-Trimethoxy-5-[2-(4-nitrophenyl)ethenyl]benzene
• CAS: 7560-41-0
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: UDXWNMYENXAKPA-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 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

• 作为反应物：
  描述：

  1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以90%的产率得到1-(4-aminophenyl)-2-(3,4,5-trimethoxyphenyl)ethane
  参考文献：
  名称：

  Inhibition of Restriction Enzymes EcoRI, BamHI and HindIII by Phenethylphenylphthalimides Derived from Thalidomide

  摘要：

  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。

  DOI：

  10.1248/cpb.59.880
• 作为产物：
  描述：

  对硝基溴化苄 在 sodium hydride 、 3-氯苯甲醛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene
  参考文献：
  名称：

  Styryl-N-phenyl-N′-(2-chloroethyl)ureas and styrylphenylimidazolidin-2-ones as new potent microtubule-disrupting agents using combretastatin A-4 as model

  摘要：

  Combretastatin A-4 (CA-4) is a well-studied and attractive molecular template to develop new antimitotics. Several thousand of modifications were performed on the ring B and the ethenyl bridge of CA-4 but only a few involved the trimethoxyphenyl moiety (TMP, ring A) often considered essential to the antiproliferative and antimicrotubule activities. In this study, we described the design, the preparation, the characterization and the biological evaluation of three new series of CA-4 analogs namely styryl-N-phenyl-N'-ethylureas (SEUs), styryl-N-phenyl-N'-(2-chloroethyl)ureas (SCEUs) and styrylphenylimidazolidin-2-ones (SIMZs) bearing a 3-Cl (series a), 3,5-Me (series b) and TMP (series c) substituents, respectively. All SCEU and SIMZ Z-isomers were active in the high and the low nanomolar range, respectively. Conversely to SEUs and their E-isomers that were significantly less active or inactive. Interestingly, the IMP moiety is giving rise to derivatives exhibiting the lowest antiproliferative activity in the SCEU series (10c) and the most active compound in the SIMZ series (12c). Moreover, SIMZ Z-isomers bearing either a 3-Cl (12a) or a 3,5-Me (12b) exhibited antiproliferative activities that are also in the same order of magnitude as 12c. All SCEU and SIMZ Z-isomers also arrested the cell cycle progression in G2/M phase, bound to the colchicine-binding site and disrupted the cytoskeleton of cancer cells. In addition to the promising and innovative microtubule-disrupting properties of SCEUs and SIMZs, these results show that the IMP moiety is not essential for the cytocidal activity of these new CA-4 analogs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.034
• 作为试剂：
  描述：

  对硝基苯乙酸 、 3,4,5-三甲氧基苯甲醛 、 哌啶 在 1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene 作用下， 以This procedure yielded a solid, 13.0 g (0.041 mol, 41%) of the desired product的产率得到1,2,3-trimethoxy-5-[2-(4-nitrophenyl)vinyl]benzene
  参考文献：
  名称：

  Method of inhibiting amyloid protein aggregation and imaging amyloid deposits

  摘要：

  本发明提供了一种使用式(I)化合物治疗阿尔茨海默病的方法。还提供了一种使用式(I)化合物抑制淀粉样蛋白聚集的方法，以及一种成像淀粉样沉积物的方法，同时还提供了新的式(I)化合物。

  公开号：

  US06972287B1

文献信息

• New two-photon absorption organic chromophores containing imino and hydroxyl groups: synthesis, ESIPT and chemosensors
  作者：Fang Gao、Xinchao Wang、Hongru Li、Xiaojuan Ye

  DOI：10.1016/j.tet.2013.04.121

  日期：2013.7

  conjugated chromophores containing imino and hydroxyl groups are presented. Excited state intramolecular proton transfer (ESIPT) of these chromophores under one- and two-photon irradiation was surveyed. One-photon absorption spectra show the presence of internal hydrogen bond in the organic dyes containing ortho-hydroxyl group, while the corresponding dyes carrying para-hydroxyl group do not exhibit intramolecular

  在这项工作中，提出了多种含有亚氨基和羟基的新型共轭生色团。调查了这些生色团在单光子和双光子照射下的激发态分子内质子转移（ESIPT）。单光子吸收光谱表明，在含有邻羟基的有机染料中存在内部氢键，而带有对羟基的相应染料则没有分子内的氢键作用。相反，在大多数非质子和质子溶剂中，带有邻羟基的扩展发色 团显示出良好分离的双发射带，斯托克斯位移大（约160 nm），而含有对羟基苯甲酸的分子-羟基基团仅显示具有正常Stokes位移（约50 nm）的单个谱带。还可以通过近红外（近红外）飞秒激光对带有邻羟基的分子观察到双光子吸收（TPA）引起的竞争性ESIPT发射。实验表明，带有邻羟基的分子在单光子和双光子激发下能够进行ESIPT，而含有对羟基的分子则没有这种特性。2-（（（3'，4'-二甲氧基-苯基亚乙基-苯基-4-ylimino）甲基）苯酚（C1）和2-（（3'，4'，5'-三甲氧基-苯基亚乙基-苯基-
• Al-containing mesoporous carbon as effective catalysts for the chemoselective reduction of carbon–carbon double bonds in nitrostilbene derivatives
  作者：Liuchang Wang、Yanjun Zheng、Xiquan Zhang、Hongmei Gu、Jiang Li、Wei Wang、Baolin Li

  DOI：10.1016/j.apcata.2013.01.040

  日期：2013.4

  reduction of carbon–carbon double bond in 4-nitrostilbene analogs bearing nitro group with hydrazine hydrate. The results indicated that the reduction reaction was able to be achieved successfully between carbon–carbon double bond and nitro group. The efficient method has been developed for the reduction of CC double bonds with diimide, catalytically generated in situ from hydrazine hydrate by the synthesized

  合成了一系列含Al，Mn，Cu和Fe的金属介孔碳催化剂，用于催化水合肼选择性还原带有硝基的4-硝基苯乙烯类似物中的碳-碳双键。结果表明，碳-碳双键与硝基之间能够成功地完成还原反应。已经开发出减少碳含量的有效方法C与二酰亚胺的双键由合成的催化剂由水合肼原位催化生成。0.15Al–MC1作为非均相催化剂在所有合成催化剂中均表现出最高的催化活性和化学选择性。在0.15Al-MC1存在下，在70°C的乙醇中，4-硝基二苯乙烯衍生物中碳-碳双键的还原率高达99％，化学选择性> 99％。另一方面，在惰性气氛下用水合肼，活性炭和FeCl 3 ·6H 2 O也容易实现4-亚硝基苯甲酸酯中硝基的高选择性还原。
• Schiemenz,G.P.; Thobe,J., Chemische Berichte, 1966, vol. 99, p. 2663 - 2668
  作者：Schiemenz,G.P.、Thobe,J.

  DOI：——

  日期：——
• Styryl-N-phenyl-N′-(2-chloroethyl)ureas and styrylphenylimidazolidin-2-ones as new potent microtubule-disrupting agents using combretastatin A-4 as model
  作者：Mathieu Gagné-Boulet、Sébastien Fortin、Jacques Lacroix、Carole-Anne Lefebvre、Marie-France Côté、René C.-Gaudreault

  DOI：10.1016/j.ejmech.2015.05.034

  日期：2015.7

  Combretastatin A-4 (CA-4) is a well-studied and attractive molecular template to develop new antimitotics. Several thousand of modifications were performed on the ring B and the ethenyl bridge of CA-4 but only a few involved the trimethoxyphenyl moiety (TMP, ring A) often considered essential to the antiproliferative and antimicrotubule activities. In this study, we described the design, the preparation, the characterization and the biological evaluation of three new series of CA-4 analogs namely styryl-N-phenyl-N'-ethylureas (SEUs), styryl-N-phenyl-N'-(2-chloroethyl)ureas (SCEUs) and styrylphenylimidazolidin-2-ones (SIMZs) bearing a 3-Cl (series a), 3,5-Me (series b) and TMP (series c) substituents, respectively. All SCEU and SIMZ Z-isomers were active in the high and the low nanomolar range, respectively. Conversely to SEUs and their E-isomers that were significantly less active or inactive. Interestingly, the IMP moiety is giving rise to derivatives exhibiting the lowest antiproliferative activity in the SCEU series (10c) and the most active compound in the SIMZ series (12c). Moreover, SIMZ Z-isomers bearing either a 3-Cl (12a) or a 3,5-Me (12b) exhibited antiproliferative activities that are also in the same order of magnitude as 12c. All SCEU and SIMZ Z-isomers also arrested the cell cycle progression in G2/M phase, bound to the colchicine-binding site and disrupted the cytoskeleton of cancer cells. In addition to the promising and innovative microtubule-disrupting properties of SCEUs and SIMZs, these results show that the IMP moiety is not essential for the cytocidal activity of these new CA-4 analogs. (C) 2015 Elsevier Masson SAS. All rights reserved.
• 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。