N-(2-chloroethyl)quinolin-4-amine | 1145669-36-8

• 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: N-(2-chloroethyl)quinolin-4-amine
• 英文别名: 4-((2-chloroethyl)amino)quinoline
• CAS: 1145669-36-8
• 化学式: C₁₁H₁₁ClN₂
• 分子量: 206.675
• InChiKey: WVTHESRGPHSRTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  N-(2-chloroethyl)quinolin-4-amine 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-((3-phenylpropyl)amino)-7-((1-(2-(quinolin-4-ylamino)ethyl)piperidin-4-yl)methoxy)-2-(4-methylpiperazin-1-yl)quinazoline
  参考文献：
  名称：

  [EN] SUBSTITUTED QUINAZOLINE DERIVATIVES AS DNA METHYLTRANSFERASE INHIBITORS
  [FR] DÉRIVÉS DE QUINAZOLINE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE L'ADN-MÉTHYLTRANSFÉRASE

  摘要：

  本发明涉及以下式(I)的化合物及其在药学上可接受的盐和溶剂化合物，它们的制备方法，它们作为药物的用途，特别是在癌症治疗中的用途，以及含有这种化合物的药物组合物。

  公开号：

  WO2016151144A1
• 作为产物：
  描述：

  7-chloro-N-(2-chloroethyl)quinolin-4-amine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到N-(2-chloroethyl)quinolin-4-amine
  参考文献：
  名称：

  一系列喹啉衍生物的合成及其体外抗结核活性

  摘要：

  合成了一系列33种喹啉衍生物，并使用Alamar Blue药敏试验评估了其对结核分枝杆菌H 37 Rv的体外抗菌活性，并以μg/ mL的最低抑菌浓度（MIC）表示了该活性。与一线药物（如乙胺丁醇）相比，化合物5e和5f分别在6.25和3.12μg/ mL处显示出显着活性，并且可能是开发新的抗多种药物耐药性先导化合物的良好起点。

  DOI：

  10.1016/j.bmc.2009.01.013

文献信息

• [EN] QUINAZOLINE DERIVATIVES AND THEIR USE AS DNA METHYLTRANSFERASE INHIBITORS<br/>[FR] DÉRIVÉS DE QUINAZOLINE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE L'ADN MÉTHYLTRANSFÉRASE
  申请人：PF MEDICAMENT

  公开号：WO2015040169A1

  公开（公告）日：2015-03-26

  The present invention relates to compounds of the following formula (I): and pharmaceutically acceptable salts and solvates thereof, their methods of preparation, their use as a drug, notably in the treatment of cancer, and pharmaceutical compositions containing such compounds.

  本发明涉及以下式（I）的化合物以及其药学上可接受的盐和溶剂化合物，它们的制备方法，它们作为药物的用途，尤其是在癌症治疗中的应用，以及含有这些化合物的药物组合物。
• QUINAZOLINE DERIVATIVES AND THEIR USE AS DNA METHYLTRANSFERASE INHIBITORS
  申请人：PIERRE FABRE MEDICAMENT

  公开号：US20160229834A1

  公开（公告）日：2016-08-11

  The present invention relates to compounds of the following formula (I): and pharmaceutically acceptable salts and solvates thereof, their methods of preparation, their use as a drug, notably in the treatment of cancer, and pharmaceutical compositions containing such compounds.

  本发明涉及以下式(I)的化合物及其药学上可接受的盐和溶剂化物，其制备方法，其作为药物的用途，尤其是在癌症治疗方面的应用，以及含有这些化合物的药物组合物。
• Substituted quinazoline derivatives as DNA methyltransferase inhibitors
  申请人：Pierre Fabre Medicament

  公开号：US10450299B2

  公开（公告）日：2019-10-22

  The present invention relates to compounds of the following formula (I) and pharmaceutically acceptable salts and solvates thereof, their methods of preparation, their use as a drug, notably in the treatment of cancer, and pharmaceutical compositions containing such compounds.

  本发明涉及下式 (I) 的化合物及其药学上可接受的盐和溶液、它们的制备方法、它们作为药物的用途（尤其是在治疗癌症方面）以及含有此类化合物的药物组合物。
• Design, biological evaluation and X-ray crystallography of nanomolar multifunctional ligands targeting simultaneously acetylcholinesterase and glycogen synthase kinase-3
  作者：Killian Oukoloff、Nicolas Coquelle、Manuela Bartolini、Marina Naldi、Rémy Le Guevel、Stéphane Bach、Béatrice Josselin、Sandrine Ruchaud、Marco Catto、Leonardo Pisani、Nunzio Denora、Rosa Maria Iacobazzi、Israel Silman、Joel L. Sussman、Frédéric Buron、Jacques-Philippe Colletier、Ludovic Jean、Sylvain Routier、Pierre-Yves Renard

  DOI：10.1016/j.ejmech.2018.12.063

  日期：2019.4

  Both cholinesterases (AChE and BChE) and kinases, such as GSK-3 alpha/beta, are associated with the pathology of Alzheimer's disease. Two scaffolds, targeting AChE (tacrine) and GSK-3 alpha/beta (valmerin) simultaneously, were assembled, using copper(I)-catalysed azide alkyne cycloaddition (CuAAC), to generate a new series of multifunctional ligands. A series of eight multi-target directed ligands (MTDLs) was synthesized and evaluated in vitro and in cell cultures. Molecular docking studies, together with the crystal structures of three MTDL/TcAChE complexes, with three tacrine-valmerin hybrids allowed designing an appropriate linker containing a 1,2,3-triazole moiety whose incorporation preserved, and even increased, the original inhibitory potencies of the two selected pharmacophores toward the two targets. Most of the new derivatives exhibited nanomolar affinity for both targets, and the most potent compound of the series displayed inhibitory potencies of 9.5 nM for human acetylcholinesterase (hAChE) and 7 nM for GSK-3 alpha/beta. These novel dual MTDLs may serve as suitable leads for further development, since, in the micromolar range, they exhibited low cytotoxicity on a panel of representative human cell lines including the human neuroblastoma cell line SH-SY5Y. Moreover, these tacrine-valmerin hybrids displayed a good ability to penetrate the blood-brain barrier (BBB) without interacting with efflux pumps such as P-gp. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Substituted Quinazoline Derivatives as DNA Methyltransferase Inhibitors
  申请人：Pierre Fabre Medicament

  公开号：US20180118717A1

  公开（公告）日：2018-05-03

  The present invention relates to compounds of the following formula (I) and pharmaceutically acceptable salts and solvates thereof, their methods of preparation, their use as a drug, notably in the treatment of cancer, and pharmaceutical compositions containing such compounds.