(4-methoxyphenyl)-(2-methylquinolin-4-yl)-amine | 6907-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (4-methoxyphenyl)-(2-methylquinolin-4-yl)-amine
• 英文别名: N-(4-methoxyphenyl)-2-methylquinolin-4-amine；4-(4-methoxyanilino)-2-methylquinoline；(4-methoxy-phenyl)-(2-methyl-quinolin-4-yl)-amine；(4-methoxy-phenyl)-(2-methyl-[4]quinolyl)-amine；(4-Methoxy-phenyl)-(2-methyl-[4]chinolyl)-amin；4-<4-Methoxy-anilino>-2-methyl-chinolin
• CAS: 6907-56-8
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: IDYPPINOEMTNLD-UHFFFAOYSA-N

物化性质

• 熔点：
  209 °C
• 沸点：
  410.5±40.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)-(2-methylquinolin-4-yl)-amine 、 N,N-二乙基-4-氨基苯甲醛 在 乙酸酐 作用下， 反应 36.0h， 以62.1%的产率得到(E)-4-(4-methoxyanilino)-2-(4-diethylamino-styryl)-quinoline
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 2-arylethenylquinoline derivatives as multifunctional agents for the treatment of Alzheimer's disease

  摘要：

  A series of new 2-arylethenylquinoline derivatives (4a(1)-4a(12), 4b(1)-4b(8), 4c(1)-4c(4), 4d(1)-4d(3) and 4e(1)-4e(9)) were designed, synthesized, and evaluated as potential multifunctional agents for the treatment of Alzheimer's disease (AD). In vitro studies showed that these synthetic compounds inhibited self-induced A beta(1-42) aggregation effectively ranged from 23.6% to 83.9% at the concentration of 20 mu M, and acted as potential antioxidants and biometal chelators. Their structure-activity relationships were obtained and discussed. In particular, compound 4b(1), the most active compound, displayed strong inhibitory activity with an IC50 value of 9.7 mu M for self-induced A beta(1-42) aggregation, good antioxidative activity with a value of 3.9-fold of Trolox, potent inhibitory activity for cholinesterase with IC50 values of 0.2 mu M and 64.1 mu M against butyrylcholinesterase (BuChE) and acetylcholinesterase (AChE), respectively. Besides, 4b(1) was also capable of disassembling the self-induced A beta(1-42) aggregation fibrils with a ratio of 59.8% at 20 mu M concentration, and had a good metal chelating activity. Taken together, these results suggest that compound 4b(1) might be a promising lead compound for AD treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.018
• 作为产物：
  描述：

  苯胺 在 对甲苯磺酸 、 三氯氧磷 作用下， 反应 14.0h， 生成 (4-methoxyphenyl)-(2-methylquinolin-4-yl)-amine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 2-arylethenylquinoline derivatives as multifunctional agents for the treatment of Alzheimer's disease

  摘要：

  A series of new 2-arylethenylquinoline derivatives (4a(1)-4a(12), 4b(1)-4b(8), 4c(1)-4c(4), 4d(1)-4d(3) and 4e(1)-4e(9)) were designed, synthesized, and evaluated as potential multifunctional agents for the treatment of Alzheimer's disease (AD). In vitro studies showed that these synthetic compounds inhibited self-induced A beta(1-42) aggregation effectively ranged from 23.6% to 83.9% at the concentration of 20 mu M, and acted as potential antioxidants and biometal chelators. Their structure-activity relationships were obtained and discussed. In particular, compound 4b(1), the most active compound, displayed strong inhibitory activity with an IC50 value of 9.7 mu M for self-induced A beta(1-42) aggregation, good antioxidative activity with a value of 3.9-fold of Trolox, potent inhibitory activity for cholinesterase with IC50 values of 0.2 mu M and 64.1 mu M against butyrylcholinesterase (BuChE) and acetylcholinesterase (AChE), respectively. Besides, 4b(1) was also capable of disassembling the self-induced A beta(1-42) aggregation fibrils with a ratio of 59.8% at 20 mu M concentration, and had a good metal chelating activity. Taken together, these results suggest that compound 4b(1) might be a promising lead compound for AD treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.018

文献信息

• Design, synthesis and biological evaluation of 4-anilinoquinoline derivatives as novel potent tubulin depolymerization agents
  作者：Yuanyuan Zhou、Wei Yan、Dong Cao、Mingfeng Shao、Dan Li、Fang Wang、Zhuang Yang、Yong Chen、Linhong He、Taijin Wang、Mingsheng Shen、Lijuan Chen

  DOI：10.1016/j.ejmech.2017.07.040

  日期：2017.9

  A series of novel 4-anilinoquinoline derivatives were synthesized and evaluated for their antiproliferative activities. Among them, 14h exhibited the most potent cytotoxic activity with IC50 values ranging from 1.5 to 3.9 nM against all tested cancer cell lines, and showed promising efficacy in multidrug resistant cancer cells. Flow cytometry assay, immune-fluorescence staining, microtubule dynamics

  合成了一系列新颖的4-苯胺基喹啉衍生物，并对其抗增殖活性进行了评估。其中，14h对所有测试的癌细胞系表现出最强的细胞毒性活性，IC 50值在1.5至3.9 nM之间，并且在多药耐药癌细胞中显示出有希望的功效。流式细胞仪分析，免疫荧光染色，微管动力学分析和EBI竞争分析通过结合秋水仙碱位点，发现14h是一种新型的微管蛋白解聚剂。重要的是，HCT116异种移植模型14h的体内功效评估显示出有效的抗肿瘤活性，而体重却没有显着下降。所有结果表明14h 可能是治疗癌症的有前途的候选人。
• Synthesis and SAR study of acridine, 2-methylquinoline and 2-phenylquinazoline analogues as anti-prion agents
  作者：H. Cope、R. Mutter、W. Heal、C. Pascoe、P. Brown、S. Pratt、B. Chen

  DOI：10.1016/j.ejmech.2006.05.002

  日期：2006.10

  Transmissible spongiform encephalopathies (TSEs) are thought to arise from aggregation of a protease resistant protein denoted PrPSc, which is a misfolded isoform of the normal cellular prion protein PrPC. Using virtual high-throughput screening we have selected structures analogous to acridine, 2-methyquinoline and 2-phenylquinazoline as potential therapeutic candidates for the treatment of TSEs. From the synthesis and screening of constructed libraries we have shown that an electron-rich aromatic ring attached through an amine linker to the position para to the ring nitrogen is beneficial to both binding to PrPC and the suppression of PrPSc accumulation for acridine and 2-methylquinoline analogues. 2-Phenylquinazoline analogues appear to utilise a different mode of action by binding at a different location and/or pose. We report IC(50)s in the nanomolar range. (c) 2006 Elsevier Masson SAS. All rights reserved.
• Microwave-Assisted Efficient Synthesis of 4-Substituted Amino-2-methylquinolines Catalyzed by p-Toluenesulfonic Acid
  作者：Xiao-qin Wang、Wen-jia Pan、Yuan-hong Cai、Xiao-yang Xie、Cui-ying Huang、Jia-yu Li、Wen-na Chen、Ming-hua He

  DOI：10.3987/com-16-13516

  日期：——

  A series of novel 4-subtituted amino-2-methylquinolines (3a-3o) were readily synthesized via the reaction of 4-chloro-2-methylquinoline with amines catalyzed by p-toluenesulfonic acid (TsoH) at 120 degrees C for 1 h under microwave-assisted organic synthesis (MAOS) condition. The yields of products 3a-3o were in range of 55-89%. This approach has advantages such as higher yield, shorter reaction time, lower costs, more convenience, and higher efficiency compared to the conventional method. The structures of the products were characterized by using H-1 NMR, C-13 NMR and HRMS. The reactivity of different amines was discussed.
• 272. 4-Anilinoquinaldine derivatives
  作者：O. G. Backeberg

  DOI：10.1039/jr9320001984

  日期：——
• 4-AMINOQUINOLINE COMPOUNDS FOR TREATING VIRUS-RELATED CONDITIONS
  申请人：Olivo Paul D.

  公开号：US20090221624A1

  公开（公告）日：2009-09-03

  This invention is directed to aminoquinoline compounds, pharmaceutical compositions of such compounds, kits comprising such compounds, and uses of such compounds for preparing medicaments and treating virus-related conditions in animals.