N'-(4-methoxy-phenyl)-N,N-dimethyl-ethylenediamine | 92058-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N'-(4-methoxy-phenyl)-N,N-dimethyl-ethylenediamine
• 英文别名: N'-(4-Methoxy-phenyl)-N,N-dimethyl-aethylendiamin；N,N-Dimethyl-N'-(4-methoxy-phenyl)-aethylendiamin；1,2-Ethanediamine, N2-(4-methoxyphenyl)-N1,N1-dimethyl-；N-(4-methoxyphenyl)-N',N'-dimethylethane-1,2-diamine
• CAS: 92058-52-1
• 化学式: C₁₁H₁₈N₂O
• mdl: MFCD09035401
• 分子量: 194.277
• InChiKey: DGUHANJFDCQQPF-UHFFFAOYSA-N

物化性质

• 沸点：
  131-133 °C(Press: 4 Torr)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(4-methoxy-phenyl)-N,N-dimethyl-ethylenediamine 生成 N-(4-methoxy-phenyl)-N',N'-dimethyl-N-(4-methyl-thiazol-2-yl)-ethylenediamine
  参考文献：
  名称：

  Fridman, Zhurnal Obshchei Khimii, 1953, vol. 23, p. 284,285

  摘要：

  DOI：
• 作为产物：
  描述：

  二甲氨基氯乙烷盐酸 、 甲氧苯胺 在 potassium carbonate 、 甲苯 作用下， 生成 N'-(4-methoxy-phenyl)-N,N-dimethyl-ethylenediamine
  参考文献：
  名称：

  Biel, Journal of the American Chemical Society, 1949, vol. 71, p. 1306,1307

  摘要：

  DOI：

文献信息

• Halogen bonding enhances activity in a series of dual 5-HT₆/D₂ ligands designed in a hybrid bioisostere generation/virtual screening protocol
  作者：Jakub Staroń、Dawid Warszycki、Rafał Kurczab、Grzegorz Satała、Ryszard Bugno、Adam Hogendorf、Andrzej J. Bojarski

  DOI：10.1039/c6ra08714k

  日期：——

  Consequently, a series of derivatives of the found hit 1d (N-[2-(dimethylamino)ethyl]-N-(2-phenylethyl)aniline) was synthesized. The most active 5-HT6/D2 ligands also showed affinity for 5-HT7R and 5-HT2AR. The para-chloroaniline derivative was identified as a potent dual 5-HT6/5-HT7 receptor antagonist (Ki = 24 nM and Kb = 30 nM, Ki = 4 nM and Kb = 1.4 nM, respectively). In the case of halogen-containing

  通过与在第二个靶标上具有活性的化合物的相似性相结合的化学空间变窄与化学空间缩小相结合的新型杂化生物等排体生成/虚拟筛选方法已成功地用于开发结构新的双5-HT 6 / D 2受体配体。因此，合成了所发现的命中1d的一系列衍生物（N- [2-（二甲基氨基）乙基] -N-（2-苯基乙基）苯胺）。最活跃的5-HT 6 / d 2点的配体也显示出对5-HT 7 R和5-HT 2A R的对位-chloroaniline衍生物被鉴定为一种有效的双重5-HT 6 /5-HT7受体拮抗剂（ K i = 24 nM和K b = 30 nM， K i = 4 nM和K b = 1.4 nM）。对于含卤素的化合物，在5-HT 6，D 2和5-HT 7受体上观察到了有趣的结构-活性关系，随后使用结合了量子极化的分子模型方法研究了配体-受体复合物配体对接（QPLD）和分子力学通用出生/表面面积（MM / GBSA）自由能计算，可以确定假定的卤素结合口袋。
• Dual Nickel/Photoredox‐Catalyzed Synthesis of <i>N</i>‐formyl <i>N</i>,<i>N’</i>‐Diaryl Ethylenediamines via Multiple C−N/C−C Coupling of Nitroarenes with Trimethylamine
  作者：Tongtong Zheng、Zhe Feng、Jun‐An Ma、Chi Wai Cheung

  DOI：10.1002/adsc.202300431

  日期：2023.7.18

  motifs in medicinal chemistry. Whereas the C−N formation reactions based on anilines and aryl halides are the most direct methods to access N,N’-diaryl ethylenediamines, the photocatalytic synthetic version remains undeveloped. Herein we describe the dual nickel/photoredox-catalyzed amination reaction using nitroarenes and trimethylamine as reaction substrates. This cascade transformation hinges on the

  N , N'-二芳基乙二胺是有机合成中的常见原料，也是药物化学中的重要结构基序。虽然基于苯胺和芳基卤化物的 CN-N 形成反应是获得N , N'-二芳基乙二胺的最直接方法，但光催化合成方法仍未开发。在此，我们描述了使用硝基芳烃和三甲胺作为反应底物的双镍/光氧化还原催化的胺化反应。这种级联转化取决于分别基于硝基芳烃和三甲胺衍生的氮自由基和α-氨甲基自由基的多个CN和CC耦合事件。各种N-甲酰基N , N'-二芳基乙二胺可以根据该反应方案获得。随后的水解提供N , N'-二芳基乙二胺用于进一步衍生化。
• Antihistaminic Agents Containing a Thiophene Nucleus
  作者：L. P. Kyrides、F. C. Meyer、F. B. Zienty、J. Harvey、L. W. Bannister

  DOI：10.1021/ja01158a026

  日期：1950.2
• Bis-aryl Urea Derivatives as Potent and Selective LIM Kinase (Limk) Inhibitors
  作者：Yan Yin、Ke Zheng、Nibal Eid、Shannon Howard、Ji-Hak Jeong、Fei Yi、Jia Guo、Chul Min Park、Mathieu Bibian、Weilin Wu、Pamela Hernandez、HaJeung Park、Yuntao Wu、Jun-Li Luo、Philip V. LoGrasso、Yangbo Feng

  DOI：10.1021/jm501680m

  日期：2015.2.26

  The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 mu M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 mu M inhibited only Limk1 and STK16 with >= 80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.
• Tertiary arylamines and process of making same
  申请人：CIBA PHARM PROD INC

  公开号：US02505133A1

  公开（公告）日：1950-04-25