(E)-1,3-二甲氧基-5-(4-硝基苯乙烯基)苯 | 586410-18-6

• 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)-1,3-二甲氧基-5-(4-硝基苯乙烯基)苯
• 英文名称: (E)-1,3-dimethoxy-5-(4-nitrostyryl)benzene
• 英文别名: trans-3,5-dimethoxy-4'-nitrostilbene；1,3-dimethoxy-5-[(E)-2-(4-nitrophenyl)ethenyl]benzene
• CAS: 586410-18-6
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: ZOKYIFYCPTXDCW-ONEGZZNKSA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  425.3±35.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1,3-二甲氧基-5-(4-硝基苯乙烯基)苯 在 sodium tetrahydroborate 、 乙醇 、 对甲苯磺酸 、 tin(ll) chloride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 4-amino-2-((4-((E)-2-(3,5-dimethoxystyryl))phenylamino)methyl)phenol
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Multitarget-Directed Resveratrol Derivatives for the Treatment of Alzheimer’s Disease

  摘要：

  A series of multitarget-directed resveratrol derivatives was designed and synthesized for the treatment of Alzheimer's disease (AD). In vitro studies indicated that most of the target compounds exhibit significant inhibition of self-induced beta-amyloid (A beta) aggregation and Cu(II)-induced A beta(1-42) aggregation and acted as potential antioxidants and biometal chelators. In particular, compounds 5d and 10d are potential lead compounds for AD therapy (5d, IC50 = 7.56 mu M and 10d, IC50 = 6.51 mu M for self-induced A beta aggregation; the oxygen radical absorbance capacity assay using fluorescein (ORAC-FL) values are 4.72 and 4.70, respectively). Moreover, these compounds are capable of disassembling the highly structured A beta fibrils generated by self- and Cu(II)-induced A beta aggregation. Furthermore, 5d crossed the blood-brain barrier (BBB) in vitro and did not exhibit any acute toxicity in mice at doses of up to 2000 mg/kg. Taken together, the data indicate that 5d is a very promising lead compound for AD.

  DOI：

  10.1021/jm400567s
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 potassium tert-butylate 、 三溴化磷 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (E)-1,3-二甲氧基-5-(4-硝基苯乙烯基)苯
  参考文献：
  名称：

  新型白藜芦醇-恶二唑杂合杂环作为潜在抗增殖剂的合成及生物学评价

  摘要：

  合成了一类新的白藜芦醇-恶二唑杂化化合物，以筛选它们对三种人类癌细胞系的体外抗增殖活性。所有化合物均显示出优于参考化合物白藜芦醇的抗增殖活性。该系列中最有希望的活性化合物是1g，2g，1c，2c，2i和1a（GI 50  <0.1 µM），具有出色的抗增殖活性。因此，我们认为白藜芦醇-恶二唑杂化化合物可能被用作开发新的抗增殖剂的良好线索。通过NMR和IR光谱数据证实了新合成的化合物的结构。

  DOI：

  10.1007/s00044-016-1514-1

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 and Bioactivity of Resveratrol Analogues
  作者：Junli Ao、Yuanmou Chen、Xiaoling Xu、Xu Zhang、Yue Yu、Peng Yu、Erbing Hua

  DOI：10.14233/ajchem.2014.16226

  日期：——

  It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.

  据报道，白藜芦醇能够增强SIRT1的表达，并通过刺激与哺乳动物SIRT1具有高度同源性的Sir2，显著模拟热量限制的效果。设计并合成了系列新型白藜芦醇衍生物，作为新型SIRT1激动剂的候选物质。通过核磁共振(1H NMR)光谱分析对合成的化合物进行了表征，并利用Bioscreen C MBR机器在100 μM/L浓度下检测了这些化合物对酵母亲本菌株BY4743的Sir2激活作用。与白藜芦醇相比，多个化合物表现出良好的Sir2激活活性。同时，还讨论了这些化合物的结构-活性关系与Sir2激活活性的相关性。
• C -2 ( E )-4-(Styryl)aniline substituted diphenylpyrimidine derivatives (Sty-DPPYs) as specific kinase inhibitors targeting clinical resistance related EGFR T790M mutant
  作者：Anran Song、Jianbin Zhang、Yang Ge、Changyuan Wang、Qiang Meng、Zeyao Tang、Jinyong Peng、Kexin Liu、Yanxia Li、Xiaodong Ma

  DOI：10.1016/j.bmc.2017.03.032

  日期：2017.5

  With the aim to overcome the drug resistance induced by the EGFR T790M mutation (EGFRT790M), herein, a family of diphenylpyrimidine derivatives (Sty-DPPYs) bearing a C-2 (E)-4-(styryl)aniline functionality were designed and synthesized as potential EGFRT790M inhibitors. Among them, the compound 10e displayed strong potency against the EGFRT790M enzyme, with the IC50 of 11.0nM. Compound 10e also showed

  为了克服由EGFR T790M突变（EGFRT790M）诱导的耐药性，本文设计并合成了具有C-2（E）-4-（苯乙烯基）苯胺官能度的二苯基嘧啶衍生物（Sty-DPPYs）家族。作为潜在的EGFRT790M抑制剂。其中，化合物10e对EGFRT790M酶具有很强的效力，IC50为11.0nM。化合物10e还显示出比罗西替尼（SI = 21.4）更高的SI值（SI = 49.0），表明其副作用较小。另外，化合物10e可以在2.91μM的浓度范围内有效抑制具有EGFRT790M突变的H1975细胞的增殖。值得注意的是，化合物10e对正常的HBE细胞毒性低（IC50 =22.48μM）。
• 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。
• One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes
  作者：Anna I. Arkhypchuk、Nicolas D’Imperio、Sascha Ott

  DOI：10.1021/acs.orglett.8b01754

  日期：2018.9.7

  MesP(Li)TMS, and an aldehyde affords Mes-phosphaalkenes which, upon methanol addition and P-oxidation, react with a second carbonyl compound site specifically to produce unsymmetric alkenes. The E/Z selectivity of the one-pot cross coupling is largely determined by the electronic nature of the aryl substituent of the first aldehyde, with electron-donating groups giving rise to increased amounts of Z-alkenes.

  锂化的仲膦MesP（Li）TMS与醛之间的磷酸-彼得森反应提供了Mes-磷烯烃，在甲醇加成和P-氧化后，Mes-磷烯烃与第二个羰基化合物位点专门反应生成不对称烯烃。一锅交叉偶联的E / Z选择性在很大程度上取决于第一醛的芳基取代基的电子性质，给电子基团导致Z-烯烃的量增加。