(E)-4-(3,4-dimethoxystyryl)aniline

• 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: (E)-4-(3,4-dimethoxystyryl)aniline
• 英文别名: 3,4-Dimethoxy-4''-amino-trans-stilbene；4-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]aniline
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: JZZHXIPQAWDZPC-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 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：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(3,4-dimethoxystyryl)aniline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以90%的产率得到4-[2-(3,4-二甲氧基苯基)乙基]苯胺
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer

  摘要：

  A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 mu M) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 mu M. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC50 1.7 mu M and 0.27 mu M, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.042
• 作为产物：
  描述：

  4-碘藜芦醚 在 四丁基溴化铵 、 potassium acetate 、 palladium diacetate 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (E)-4-(3,4-dimethoxystyryl)aniline
  参考文献：
  名称：

  基于龙血中支架的成人海马神经发生有效刺激物的发现

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2017.05.025

文献信息

• Design, Synthesis, and Antitumor Activity of Novel Quinazoline Derivatives
  作者：Liuchang Wang、Pengna Li、Baolin Li、Yawen Wang、Jiangtao Li、Limei Song

  DOI：10.3390/molecules22101624

  日期：——

  epidermal growth factor receptor (EGFR) inhibitors, novel 4-stilbenylamino quinazoline derivatives were synthesized through a Dimorth rearrangement reaction and characterized via IR, 1H-NMR, 13C-NMR, and HRMS. Methoxyl, methyl, halogen, and trifluoromethyl groups on stilbeneamino were detected. These synthesized compounds were evaluated for antitumor activity in vitro against eight human tumor cell lines

  为了探索一类新的表皮生长因子受体 (EGFR) 抑制剂，通过 Dimorth 重排反应合成了新型 4-芪氨基喹唑啉衍生物，并通过 IR、1H-NMR、13C-NMR 和 HRMS 进行表征。检测到芪氨基上的甲氧基、甲基、卤素和三氟甲基。使用 MTS 测定法评估了这些合成化合物对八种人肿瘤细胞系的体外抗肿瘤活性。大多数合成的化合物对 A431、A549 和 BGC-823 细胞系表现出比吉非替尼 (IC50 > 10.0 μM) 更强的活性 (IC50 = ~2.0 μM)。进行化合物6c和6i结合到EGFR的ATP位点的对接方法。结果表明，氟和三氟甲基在有效的细胞活性中起重要作用。
• Non-linear and potential non-linear optical materials containing molybdenum or tungsten mononitrosyl redox centres. Stilbene derivatives containing ferrocenyl, methoxy or dimethylamino donor groups
  作者：Benjamin J. Coe、Thomas A. Hamor、Christopher J. Jones、Jon A. McCleverty、David Bloor、Graham H. Cross、Tony L. Axon

  DOI：10.1039/dt9950000673

  日期：——

  Kurtz powder test for second harmonic generation (SHG). The ferrocenyl derivatives have been found to exhibit SHG on irradiation at 1907 nm, whereas all of the derivatives containing NMe2 or OMe groups are SHG inactive. The crystal structure of [Mo(NO)HB(dmpz)3}ClOC6H4[CHCHC6H4(NMe2-4)]-4}] shows that, although the compound crystallises in a polar space group, the lattice contains pseudocentrosymmetrically

  化合物[M（NO）HB（dmpz）3 } X n EC 6 H 4（CH CHC 6 H 3 –R，R'）-4} 2- n ]（dmpz = 3,5-二甲基吡唑基，n = 1，E = NH，R = [（η 5 -C 5 H ^ 4）的Fe（η 5 -C 5 H ^ 5）] - 4，R'= H; E = O，R = R'= H，E ＝ O或NH，R ＝ 4-OMe，R′＝ H； R ＝ 4-NMe 2，R′＝ H； E ＝ NH，R ＝ 2-OMe，R′＝ 4-OMe； R ＝ 3-OMe ，R'= 4-OMe； R = 2-OMe，R'= 5-OMe； M = Mo，X = Cl或I； M = W，X = Cl；n = 2； E = O，R = R ′= H; E = O或NH，R = 4-OMe或-NMe 2，R′＝ H；E = NH，R = 2-OMe，R'= 4-OMe; R ＝
• Discovery of a novel lead characterized by a stilbene-extended scaffold against sepsis as soluble epoxide hydrolase inhibitors
  作者：Zi-Qiang Feng、Jing Ding、Min-Zhen Zhu、Wei-Song Xie、Rui-Chen Liu、Si-Si Liu、Si-Meng Liu、Ming-Jia Yu、Xin-Hong Zhu、Jian-Hua Liang

  DOI：10.1016/j.ejmech.2023.116113

  日期：2024.2

  Recently, some inhibitors of soluble epoxide hydrolase (sEH) showed limited potential in treating sepsis by increasing survival time, but they have unfortunately failed to improve survival rates. In this study, we initially identified a new hit , belonging to a natural skeleton known as stilbene and having an IC of 644 nM on inhibiting murine sEH. Natural scaffold-based sEH inhibitors are paid less

  最近，一些可溶性环氧化物水解酶（sEH）抑制剂通过延长生存时间来治疗脓毒症的潜力有限，但不幸的是它们未能提高生存率。在这项研究中，我们最初鉴定了一个新的靶点，属于一种名为二苯乙烯的天然骨架，抑制小鼠 sEH 的 IC 值为 644 nM。基于天然支架的 sEH 抑制剂受到的关注较少。构效关系 (SAR) 引导的结构优化和计算机辅助骨架生长的结合产生了高效的先导化合物 (IC50: 4.0 nM)。剂量反应研究表明（腹腔注射剂量为 0.5-5 mg/kg）可通过降低肝脏中炎症因子 TNF-α 和 IL-6 的水平显着提高存活率和存活时间。有趣的是，肝脏中的蓄积量远高于血浆中的蓄积量（AUC 比率：175）。此外，在抑制人 sEH 方面，其 IC50 值 (1.5 nM) 与 EC5026 (1.7 nM) 相同。总之，天然支架延伸的 sEH 抑制剂有潜力成为解决脓毒症治疗中未满足的医疗需求的
• Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents
  作者：Jun Yan、Yueyan Guo、Yali Wang、Fei Mao、Ling Huang、Xingshu Li

  DOI：10.1016/j.ejmech.2015.03.030

  日期：2015.5

  To identify novel multi-target-directed drug candidates for the treatment of cancer, a series of benzoselenazole-stilbene hybrids were synthesised by combining the pharmacophores of resveratrol and ebselen. The biological assay indicated that all of the hybrids exhibited antiproliferative activities against four human cancer cell lines and demonstrated good TrxR inhibitory activities. The mechanism of cell apoptosis was investigated in G2/M cell cycle arrest induced by compound 6e and the apoptosis of the human liver carcinoma Bel-7402 cell line. The significant increase in intracellular ROS confirmed that compound 6e was capable of causing oxidative stress-induced apoptosis in cancer cells. Our results support the potential of compound 6e as a candidate for further studies examining the development of novel drugs for cancer treatment. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Separation of α-glucosidase-inhibitory and liver X receptor-antagonistic activities of phenethylphenyl phthalimide analogs and generation of LXRα-selective antagonists
  作者：Kazunori Motoshima、Tomomi Noguchi-Yachide、Kazuyuki Sugita、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1016/j.bmc.2009.05.066

  日期：2009.7

  Liver X receptor (LXR) alpha/beta dual agonists are candidate medicaments for the treatment of metabolic syndrome, because their biological actions include increasing cholesterol efflux mediated by LXR beta. However, their clinical application is currently limited by their enhancing effect on triglyceride (TG) synthesis mediated by LXR alpha. Combination of an LXR alpha-selective antagonist with an LXR alpha/beta dual agonist may overcome this disadvantage. In the present work, structural development studies of phenethylphenyl phthalimide 9, which possesses LXR alpha/beta dual-antagonistic activity and alpha-glucosidase-inhibitory activity, led to the LXR alpha-selective antagonist 23f. Specific alpha-glucosidase inhibitors were also obtained. (C) 2009 Elsevier Ltd. All rights reserved.