(2-aminophenyl)-[(2-methoxyphenyl)methyl]amine | 7192-08-7

• 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: (2-aminophenyl)-[(2-methoxyphenyl)methyl]amine
• 英文别名: N-(2-Methoxy-benzyl)-benzene-1,2-diamine；2-N-[(2-methoxyphenyl)methyl]benzene-1,2-diamine
• CAS: 7192-08-7
• 化学式: C₁₄H₁₆N₂O
• mdl: MFCD11187037
• 分子量: 228.294
• InChiKey: RXDLHXPFPJZQLK-UHFFFAOYSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  386.1±27.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  47.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-aminophenyl)-[(2-methoxyphenyl)methyl]amine 在 碳酸氢钠 作用下， 以 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 以20 g (50%)的产率得到1-{[2-(chloromethyl)benzimidazolyl]methyl}-2-methoxybenzene
  参考文献：
  名称：

  Aryl and hetroaryl fused aminoalkyl-imidazole derivatives: selective modulators of bradykinin B2 receptors

  摘要：

  揭示了以下分子的化学式：或其在药学上可接受的非毒性盐中，其中：A、B、C 和 D 为 N 或 CH；X 为键合或（未）取代的 CH2；R1 为较低的烯烃基或（未）取代的较低的烷基；R3 为较低的烷基；R2、R4、R5 和 R6 是在此处定义的变量；这些化合物在诊断和治疗肾脏疾病、心力衰竭、高血压、美尼尔氏病、阴道炎症和疼痛、周围循环障碍、更年期紊乱、视网膜脉络膜循环障碍、心肌缺血、心肌梗死、心肌梗死后综合征、心绞痛、经皮冠状动脉成形术后再狭窄、肝炎、肝硬化、胰腺炎、肠梗阻、糖尿病、糖尿病并发症、男性不育或青光眼，或用于增加血脑屏障的通透性、疼痛、哮喘和鼻炎的治疗中具有用处。

  公开号：

  US06358949B1
• 作为产物：
  描述：

  N-[1-(2-Methoxy-phenyl)-meth-(E)-ylidene]-benzene-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.5h， 以0.35 g的产率得到(2-aminophenyl)-[(2-methoxyphenyl)methyl]amine
  参考文献：
  名称：

  Hydrogen-Bond-Driven Electrophilic Activation for Selectivity Control: Scope and Limitations of Fluorous Alcohol-Promoted Selective Formation of 1,2-Disubstituted Benzimidazoles and Mechanistic Insight for Rationale of Selectivity

  摘要：

  Hydrogen-bond-driven electrophilic activation for selectivity control during competitive formation of 1,2-disubstituted and 2-substituted benzimidazoles from o-phenylenediamine and aldehydes is reported. The fluorous alcohols trifluoroethanol and hexafluoro-2-propanol efficiently promote the cyclocondensation of o-phenylenediamine with aldehydes to afford selectively the 1,2-disubstituted benzimidazoles at rt in short times. A mechanistic insight is invoked by NMR, mass spectrometry, and chemical studies to rationalize the selectivity. The ability of the fluorous alcohols in promoting the reaction and controlling the selectivity can be envisaged from their better hydrogen bond donor (HBD) abilities compared to that of the other organic solvents as well as of water. Due to the better HBD values, the fluorous alcohols efficiently promote the initial bisimine formation by electrophilic activation of the aldehyde carbonyl. Subsequently the hydrogen-bond-mediated activation of the in situ-formed bisimine triggers the rearrangement via 1,3-hydride shift to form the 1,2-disubstituted benzimidazoles.

  DOI：

  10.1021/jo301793z

文献信息

• 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
• Melanin concentrating hormone receptor ligands: substituted 2-(4-benzyl-piperazin-1-ylmethyl)- and 2-(4-benzyl-diazepan-1-ylmethyl)-1H-benzoimidazole analogues
  申请人：——

  公开号：US20030229074A1

  公开（公告）日：2003-12-11

  Melanin concentrating hormone receptor ligands (especially substituted 2-(4-benzyl-piperazin-1-ylmethyl)-1H-benzoimidazole analogues), capable of modulating MCH receptor activity, are provided. Such ligands may be used to modulate MCH binding to MCH receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of metabolic, feeding and sexual disorders in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such ligands for detecting MCH receptors (e.g., receptor localization studies).

  提供了黑色素浓缩激素受体配体（特别是取代的2-(4-苄基-哌嗪-1-基甲基)-1H-苯并咪唑类似物），能够调节MCH受体活性。这些配体可用于调节MCH与体内或体外的MCH受体结合，并在治疗人类、驯养伴侣动物和家畜动物的多种代谢、进食和性功能障碍方面特别有用。还提供了用于治疗这些障碍的药物组合物和方法，以及用于检测MCH受体的配体的方法（例如，受体定位研究）。
• Aryl and heteroaryl fused aminoalkyl-imidazole derivatives: selective modulators of bradykinin B2 receptors
  申请人：Neurogen Corporation

  公开号：US20020151550A1

  公开（公告）日：2002-10-17

  Disclosed are compounds of the formula: 1 or the pharmaceutically acceptable non-toxic salts thereof wherein: A, B, C. and D are N or CH; X is a bond or (un)substituted CH 2 ; R 1 is lower alkenyl or (un)substituted lower alkyl; R 3 is lower alkyl; and R 2 , R 4 , R 5 , and R 6 are variables defined herein; which compounds are useful in the diagnosis and treatment of renal diseases, heart failure, hypertension, Meniere's disease, vaginal inflammation and pain, peripheral circulatory disorders, climacteric disturbance, retinochoroidal circulatroy disorders, myocardial ischemia, myocardial infarction, postmyocardial infarction syndrome, angina pectoris, restenosis after percutaneous transluminal coronary angioplasty, hepatitis, liver cirrhosis, pancreatitis, ileus, diabetes, diabetic complications, male infertility or glaucoma, or for the increase of permeability of blood-brain barrier, pain, asthma, and rhinitis.

  公开的是以下化合物的结构式：1或其药学上可接受的非毒性盐，其中：A、B、C和D为N或CH；X为键或（未）取代的CH2；R1为较低的烯基或（未）取代的较低烷基；R3为较低的烷基；R2、R4、R5和R6为本文中定义的变量；这些化合物在肾脏疾病、心力衰竭、高血压、梅尼埃病、阴道炎症和疼痛、周围循环障碍、更年期障碍、视网膜脉络膜循环障碍、心肌缺血、心肌梗死、心肌梗死后综合征、心绞痛、经皮冠状动脉成形术后再狭窄、肝炎、肝硬化、胰腺炎、肠梗阻、糖尿病、糖尿病并发症、男性不育症或青光眼的诊断和治疗中有用，或用于增加血脑屏障的通透性、疼痛、哮喘和鼻炎。
• 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.
• BENZIMIDAZOLE AND IMIDAZOLOPYRIDINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS SELECTIVE MODULATORS OF BRADYKININ B2 (= BK-2) RECEPTORS
  申请人：NEUROGEN CORPORATION

  公开号：EP1165518A2

  公开（公告）日：2002-01-02