N-[2-(3,4-dimethoxyphenyl)ethyl]benzene-1,2-diamine | 5761-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(3,4-dimethoxyphenyl)ethyl]benzene-1,2-diamine
• 英文别名: N-(3,4-Dimethoxy-phenylaethyl)-o-phenylendiamin；N-(3,4-Dimethoxy-phenaethyl)-o-phenylendiamin；N1-(3,4-dimethoxyphenethyl)benzene-1,2-diamine；2-N-[2-(3,4-dimethoxyphenyl)ethyl]benzene-1,2-diamine
• CAS: 5761-37-5
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: BKTXIZUTZYIZOD-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C
• 沸点：
  460.3±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  四氧嘧啶 、 N-[2-(3,4-dimethoxyphenyl)ethyl]benzene-1,2-diamine 在 硼酸 、 溶剂黄146 作用下， 以84%的产率得到10-(3,4-dimethoxyphenethyl)benzo[g]pteridine-2,4(3H,10H)-dione
  参考文献：
  名称：

  Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis

  摘要：

  This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). These compounds exhibited high activity against both the enzymes AChE as well as BuChE. Of the synthesized compounds, the most potent isoalloxazine derivatives (7m and 7q) showed IC50 values of 4.72 mu M and 5.22 mu M respectively against AChE; and, 6.98 mu M and 5.29 mu M respectively against BuChE. These two compounds were further evaluated for their anti-aggregatory activity for beta-amyloid (A beta) in presence and absence of AChE by performing Thioflavin-T (ThT) assay and Congo red (CR) binding assay. In order to evaluate cytotoxic profile of these two potential compounds, cell viability assay of SH-SY5Y human neuroblastoma cells was performed. Further, to understand the binding behavior of these two compounds with AChE and BuChE enzymes, docking studies have been reported. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.05.005
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 生成 N-[2-(3,4-dimethoxyphenyl)ethyl]benzene-1,2-diamine
  参考文献：
  名称：

  Synthesen von Chinoxalin-Derivaten †

  摘要：

  Es werden在1-Stellung苄基和苯基thyyrlierte 3-Benzyl-1,2-dihydrochinoxalin-2-one，1,6,7-trisubituierte 1,2-Dihydrochinoxalin-2-one和-3-Methyldihydrochinoxalin-2-one，verätherte 2-羟基-喹喔啉，1,2,3,4-四氢喹喔啉和苯并四氢呋喃衍生物，药代动力学合成法。

  DOI：

  10.1002/hlca.19660490214

文献信息

• Synthesen von Chinoxalin-Derivaten
  作者：H. Zellner、G. Zellner

  DOI：10.1002/hlca.19660490214

  日期：1966.3.10

  Es werden in 1-Stellung benzylierte und phenyläthylierte 3-Benzyl-1,2-dihydrochinoxalin-2-one, 1,6,7-trisubstituierte 1,2-Dihydrochinoxalin-2-one und -3-Methyldihydrochinoxalin-2-one, verätherte 2-Hydroxy-chinoxaline, sowie 1,2,3,4-Tetrahydrochinoxaline und deren Quartärisate beschrieben, die zwecks pharmakologischer Prüfung synthetisiert wurden.

  Es werden在1-Stellung苄基和苯基thyyrlierte 3-Benzyl-1,2-dihydrochinoxalin-2-one，1,6,7-trisubituierte 1,2-Dihydrochinoxalin-2-one和-3-Methyldihydrochinoxalin-2-one，verätherte 2-羟基-喹喔啉，1,2,3,4-四氢喹喔啉和苯并四氢呋喃衍生物，药代动力学合成法。
• A Practical Oxone®-Mediated,High-Throughput, Solution-Phase Synthesis of Benzimidazolesfrom 1,2-Phenylenediamines and Aldehydes and its Application toPreparative Scale Synthesis
  作者：Pierre Beaulieu、Bruno Haché、Elisabeth von Moos

  DOI：10.1055/s-2003-40888

  日期：2003.8

  Addition of oxone® to a mixture of a 1,2-phenylenediamine and an aldehyde in wet DMF at room temperature results in rapid formation of benzimidazoles under very mild conditions. The reaction is applicable to a wide range of substrates including aliphatic, aromatic and heteroaromatic aldehydes, and is not significantly affected by steric or electronic effects. In most cases, crude products are isolated in good to excellent yields (59-95%) and homogeneities (86-99%) by simple precipitation or extraction from the reaction mixture and do not require additional purification. Limitations to the scope of this methodology were encountered in cases where aldehydes were sensitive to oxone® under the acidic reaction conditions. The features of this methodology make it particularly well suited for the high-throughput, solution-phase synthesis of benzimidazole libraries. The low cost and simplicity of this procedure makes it equally attractive for preparative-scale syntheses where safety and environmental issues are of greater concern.

  在室温下，将oxone®添加到1,2-苯二胺和醛的湿DMF混合物中，可以在非常温和的条件下快速形成苯并咪唑。该反应适用于多种底物，包括脂肪族、芳香族和杂芳香族醛，并且不受立体或电子效应的显著影响。在大多数情况下，粗产物通过简单的沉淀或从反应混合物提取，得到了良好至优异的产率（59-95%）和均匀性（86-99%），且不需要额外的纯化。该方法的适用范围在某些对oxone®在酸性反应条件下敏感的醛的情况下受到限制。这种方法的特点使其特别适合于苯并咪唑库的高通量溶液相合成。该程序的低成本和简单性也使其在对安全和环境问题更为关注的制备规模合成中同样具有吸引力。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS DE L'HISTONE DESACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2006102760A1

  公开（公告）日：2006-10-05

  [EN] This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula (I); wherein Y, L, Z, W, X, Q, R₁, R₂ and R₃ are as defined in the specification.
  [FR] L'invention concerne des composés inhibiteurs de l'histone-désacétylase. L'invention concerne en particulier des composés représentés par la formule (I) dans laquelle Y, L, Z, W, X, Q, R₁, R₂ et R₃ sont tels que définis dans les spécifications.
• Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis
  作者：Ashish M. Kanhed、Anshuman Sinha、Jatin Machhi、Ashutosh Tripathi、Zalak S. Parikh、Prakash P. Pillai、Rajani Giridhar、Mange Ram Yadav

  DOI：10.1016/j.bioorg.2015.05.005

  日期：2015.8

  This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). These compounds exhibited high activity against both the enzymes AChE as well as BuChE. Of the synthesized compounds, the most potent isoalloxazine derivatives (7m and 7q) showed IC50 values of 4.72 mu M and 5.22 mu M respectively against AChE; and, 6.98 mu M and 5.29 mu M respectively against BuChE. These two compounds were further evaluated for their anti-aggregatory activity for beta-amyloid (A beta) in presence and absence of AChE by performing Thioflavin-T (ThT) assay and Congo red (CR) binding assay. In order to evaluate cytotoxic profile of these two potential compounds, cell viability assay of SH-SY5Y human neuroblastoma cells was performed. Further, to understand the binding behavior of these two compounds with AChE and BuChE enzymes, docking studies have been reported. (C) 2015 Elsevier Inc. All rights reserved.
• Indoloquinoxaline derivatives as promising multi-functional anti-Alzheimer agents
  作者：Ashish M. Kanhed、Dushyant V. Patel、Nirav R. Patel、Anshuman Sinha、Priyanka S. Thakor、Kishan B. Patel、Navnit K. Prajapati、Kirti V. Patel、Mange Ram Yadav

  DOI：10.1080/07391102.2020.1840441

  日期：2022.4.13

  Abstract To confront a disease like Alzheimer’s disease having complex pathogenesis, development of multitarget-directed ligands has emerged as a promising drug discovery approach. In our endeavor towards the development of multitarget-directed ligands for Alzheimer’s disease, a series of indoloquinoxaline derivatives were designed and synthesized. In vitro cholinesterase inhibition studies revealed

  摘要 为了对抗阿尔茨海默病等具有复杂发病机制的疾病，多靶点定向配体的开发已成为一种有前途的药物发现方法。在我们致力于开发针对阿尔茨海默病的多靶点定向配体的过程中，设计并合成了一系列吲哚喹喔啉衍生物。体外胆碱酯酶抑制研究表明，所有合成的化合物都表现出中等至良好的胆碱酯酶抑制活性。6-(6-(Piperidin-1-yl)hexyl)-6 H -indolo[2,3- b ]quinoxaline 9f被确定为最有效和选择性的 BuChE 抑制剂 (IC 50= 0.96 µM，选择性指数 = 0.17)，与商业批准的参考药物多奈哌齐 (IC 50 = 1.87 µM)相比，BuChE 抑制活性高出 2 倍。此外，化合物9f还具有自诱导 Aβ 1-42聚集抑制活性（在 50 μM 浓度下抑制 51.24%）。该系列的一些化合物也显示出适度的抗氧化活性。为了解化合物9f的推定结合模式，进行了分子