4-anilino-2-methylquinoline | 51336-03-9

• 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-anilino-2-methylquinoline
• 英文别名: 4-Phenylamino-2-methylquinoline；2-methyl-N-phenylquinolin-4-amine
• CAS: 51336-03-9
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: BCRJMTYTLWCQKO-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  377.5±27.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-anilino-2-methylquinoline 在 硫酸 、 碘 作用下， 以 甲醇 、 苯 为溶剂， 反应 48.0h， 以65%的产率得到6-methyl-11H-indolo<3,2-c>quinoline
  参考文献：
  名称：

  杂原子定向的光环化：吲哚喹啉生物碱的合成：隐地平，隐花果碱，隐血人扁豆碱及其甲基衍生物

  摘要：

  描述了吲哚喹啉生物碱的三步合成。2，3和4-取代的卤代喹啉与苯胺的反应得到各自的苯胺喹啉，其在光环化后得到吲哚喹啉。通过在喹啉氮上的区域选择性甲基化，提供了生物碱隐tackieine，隐sanguinolentine，隐lepinepine和合成异构体isooneocryptolepine。还合成了它们的甲基衍生物，以寻找新的抗疟原虫药物和DNA嵌入剂。

  DOI：

  10.1016/j.tet.2006.04.050
• 作为产物：
  描述：

  4-羟基-2-甲基喹啉 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-anilino-2-methylquinoline
  参考文献：
  名称：

  杂原子定向的光环化：吲哚喹啉生物碱的合成：隐地平，隐花果碱，隐血人扁豆碱及其甲基衍生物

  摘要：

  描述了吲哚喹啉生物碱的三步合成。2，3和4-取代的卤代喹啉与苯胺的反应得到各自的苯胺喹啉，其在光环化后得到吲哚喹啉。通过在喹啉氮上的区域选择性甲基化，提供了生物碱隐tackieine，隐sanguinolentine，隐lepinepine和合成异构体isooneocryptolepine。还合成了它们的甲基衍生物，以寻找新的抗疟原虫药物和DNA嵌入剂。

  DOI：

  10.1016/j.tet.2006.04.050

文献信息

• Anticancer-Active <i>N</i>-Heteroaryl Amines Syntheses: Nucleophilic Amination of <i>N</i>-Heteroaryl Alkyl Ethers with Amines
  作者：Xia Wang、Qiu-Xia Yang、Cheng-Yu Long、Yan Tan、Yi-Xin Qu、Min-Hui Su、Si-Jie Huang、Weihong Tan、Xue-Qiang Wang

  DOI：10.1021/acs.orglett.9b01711

  日期：2019.7.5

  A mild amination protocol of N-heteroaryl alkyl ethers with various amines is described. This transformation is achieved by utilizing simple and readily available base as promoter via C–O bond cleavage, offering a new amination strategy to access several anticancer-active compounds. This work is highlighted by the excellent functional group compatibility, scalability, wide substrate scope, and easy

  描述了N-杂芳基烷基醚与各种胺的温和胺化方案。通过使用简单易用的碱基作为启动子通过C–O键裂解来实现这种转化，从而提供了一种新的胺化策略来使用多种抗癌活性化合物。出色的官能团兼容性，可扩展性，广泛的底物范围以及多种药物的容易衍生化，突出了这项工作。
• Synthesis of Novel Alkyl and Aryl Substituted Dibenzo[<i>b,h</i>][1,6]naphthyridines
  作者：M. Manoj、K. J. Rajendra Prasad

  DOI：10.1080/00397911.2010.525336

  日期：2012.2.1

  one-pot synthesis of 7-alkyl and aryl substituted dibenzo[b,h][1,6]naphthyridines is reported from the reaction of 4-chloro-2-methylquinolines and alkyl/aryl substituted aminoketones. Because the yield of the dibenzonaphthyridines was poor, in an alternative method the title compounds were prepared from the 4-chloro-2-methylquinolines via anilinoquinolines as intermediates employing alkyl and aryl carboxylic

  摘要 4-氯-2-甲基喹啉与烷基/芳基取代的氨基酮反应，一锅法合成了7-烷基和芳基取代的二苯并[b,h][1,6]萘啶。由于二苯并萘啶的产率很低，在替代方法中，标题化合物是由 4-氯-2-甲基喹啉通过苯胺喹啉作为中间体使用烷基和芳基羧酸制备的，这提高了产率。图形概要
• PHENYL N-MUSTARD LINKED TO DNA-AFFINIC MOLECULES OR WATER-SOLUBLE ARYL RINGS, METHOD AND THEIR USE AS CANCER THERAPEUTIC AGENTS
  申请人：SU Tsann-Long

  公开号：US20130178494A1

  公开（公告）日：2013-07-11

  The present disclosure relates to new DNA-directed alkylating agents and water-soluble N-mustard agents with improved chemical stability and anti-tumor therapeutic efficacy.

  本公开涉及新的DNA定向烷基化剂和具有改善化学稳定性和抗肿瘤治疗效果的水溶性N-芥子剂。
• 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.