2-氨基-4-氯喹啉 | 20151-42-2

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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
• 中文名称: 2-氨基-4-氯喹啉
• 英文名称: 4-chloroquinolin-2-amine
• 英文别名: 2-amino-4-chloroquinoline；4-chloro-quinolin-2-ylamine
• CAS: 20151-42-2
• 化学式: C₉H₇ClN₂
• mdl: MFCD08705642
• 分子量: 178.621
• InChiKey: WHFKEBBQPCDRND-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  327.3±22.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-氨基-4-氯喹啉 以 水 为溶剂， 生成 N⁴,N⁴-Dimethylquinoline-2,4-diamine
  参考文献：
  名称：

  BENZOTHIOPHENE DERIVATIVE

  摘要：

  [待解决问题] 旨在提供一种具有PDE10A抑制活性的化合物，并具有新颖结构，或其同位素或药用可接受盐，以及一种以该化合物作为活性成分的药物组合物。 [解决方案] 本发明提供了一种由通用公式（I）表示的化合物或其药用可接受盐。

  公开号：

  US20160024060A1
• 作为产物：
  描述：

  4-氯喹啉-N-氧化物 在 4-甲苯磺酸酐 、 叔丁胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以1.10 g的产率得到2-氨基-4-氯喹啉
  参考文献：
  名称：

  Developing Inhibitors of the p47phox–p22phox Protein–Protein Interaction by Fragment-Based Drug Discovery

  摘要：

  Nicotinamide adenine dinucleotide phosphate oxidase isoform 2 is an enzyme complex, which generates reactive oxygen species and contributes to oxidative stress. The p47phox-p22phox interaction is critical for the activation of the catalytical NOX2 domain, and p47phox is a potential target for therapeutic intervention. By screening 2500 fragments using fluorescence polarization and a thermal shift assay and validation by surface plasmon resonance, we found eight hits toward the tandem SH3 domain of p47phox (p47phox(SH3A-B)) with K-D values of 400-600 mu M. Structural studies revealed that fragments 1 and 2 bound two separate binding sites in the elongated conformation of p47phox(SH3A-B) and these competed with p22phox for binding to p47phox(SH3A-B). Chemical optimization led to a dimeric compound with the ability to potently inhibit the p47phox(SH3A-B)-p22phox interaction (K-i of 20 mu M). Thereby, we reveal a new way of targeting p47phox and present the first report of drug-like molecules with the ability to bind p47phox and inhibit its interaction with p22phox.

  DOI：

  10.1021/acs.jmedchem.9b01492

文献信息

• [EN] SMALL-MOLECULE NADPH OXIDASE 2 INHIBITORS<br/>[FR] INHIBITEURS DE NADPH OXYDASE 2 À PETITE MOLÉCULE
  申请人：UNIV COPENHAGEN

  公开号：WO2021105497A1

  公开（公告）日：2021-06-03

  The invention provides compounds of Formula (II) which comprise two terminal 2-aminoquinoline moieties. They are novel and potent inhibitors of the p47phox-p22phox protein-protein interaction that can inhibit the assembly and thus activation of the multisubunit and superoxide-generating NADPH oxidase 2 complex. The compounds are therapeutically relevant as they can reduce cell damage in diseases where NADPH oxidase 2 is a major contributor to generation of reactive oxygen species (ROS) and oxidative stress.

  该发明提供了公式（II）的化合物，其中包括两个末端的2-氨基喹啉基团。它们是新颖且有效的 p47phox-p22phox 蛋白质相互作用抑制剂，可以抑制多亚基和产生超氧化物的 NADPH 氧化酶 2 复合物的组装和激活。这些化合物在治疗上具有重要意义，因为它们可以减少 NADPH 氧化酶 2 在产生活性氧物种（ROS）和氧化应激中起主要作用的疾病中的细胞损伤。
• Phenyl, Pyridine, Quinoline, Isoquinoline, Naphthyridine and Pyrazine Derivatives
  申请人：Binggeli Alfred

  公开号：US20080045544A1

  公开（公告）日：2008-02-21

  This invention is concerned with compounds of the formula and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.

  这项发明涉及公式的化合物及其药用盐。该发明还涉及含有这种化合物的药物组合物，以及用于制备它们的过程以及它们用于治疗和/或预防与调节SST受体亚型5相关的疾病的用途。
• A convenient one-pot Negishi coupling of amino-heteroaryl chlorides and alkyl bromides
  作者：Iain A.S. Walters

  DOI：10.1016/j.tetlet.2005.11.013

  日期：2006.1

  A simple Ni-catalysed cross-coupling protocol for amino-heteroaryl chlorides with alkylzinc reagents has been developed. The alkylzinc reagents can be commercially available dialkylzincs or alkylzinc halides, or can be conveniently generated in situ from diethylzinc and primary alkyl bromides in the presence of the same inexpensive Ni catalyst used to effect the subsequent coupling reaction.

  已经开发了一种简单的Ni催化的氨基杂芳基氯化物与烷基锌试剂的交叉偶联方案。烷基锌试剂可以是可商购的二烷基锌或卤化烷基锌，或者可以在与用于进行后续偶联反应相同的廉价Ni催化剂的存在下方便地由二乙基锌和伯烷基溴化物原位产生。
• PHOSPHOROUS DERIVATIVES AS KINASE INHIBITORS
  申请人：ARIAD PHARMACEUTICALS, INC.

  公开号：US20150225436A1

  公开（公告）日：2015-08-13

  The invention features compounds of the general formula: in which the variable groups are as defined herein, and to their preparation and use.

  该发明涉及一般式化合物：其中变量基团如本文所定义，以及它们的制备和使用。
• [EN] A3 ADENOSINE RECEPTOR ALLOSTERIC MODULATORS<br/>[FR] MODULATEURS ALLOSTÉRIQUES DU RÉCEPTEUR DE L'ADÉNOSINE A3
  申请人：UNIV LEIDEN

  公开号：WO2010020981A1

  公开（公告）日：2010-02-25

  The present invention provides 2,4-disubstituted quinoline derivatives being an A3 adenosine receptor modulator (A3RM), for use in the treatment of a condition which is treatable by adenosine, an A3 adenosine receptor (A3AR) agonist or an A3 adenosine receptor antagonist. In one embodiment, the 2,4-disubstituted quinoline derivatives are for use in the treatment of a condition treatable by an adenosine or an A3AR agonist, treatment being achieved by enhancing activity of a protein (by binding of said 2,4 disubstituted quinoline derivative to the A3AR). Some conditions treatable by the 2,4 disubstituted quinoline derivative when used for enhancing activity include, malignancy, an immuno-compromised affliction, high intraocular pressure or a condition associated with high intraocular pressure. The invention also provides method for treatment of a subject having a condition treatable by adenosine, an A3AR agonist or an A3AR antagonist making use of the defined 2,4-disubstituted quinoline derivative (s), and pharmaceutical composition and comprising said derivative and a kit comprising the derivative and instructions for use thereof. One specific 2,4-disubstituted quinoline derivative comprises N-2-[(3,4-dichlorophenyl)amino]quinolin-4-yl}cyclohexanecarboxamide In one embodiment, the 2,4-disubstituted quinoline derivatives in accordance with the invention are formulated in a form suitable for oral administration.

  本发明提供了2,4-二取代喹啉衍生物，作为A3腺苷受体调节剂（A3RM），用于治疗可通过腺苷、A3腺苷受体（A3AR）激动剂或A3腺苷受体拮抗剂治疗的病症。在一个实施例中，2,4-二取代喹啉衍生物用于治疗可通过腺苷或A3AR激动剂治疗的病症，通过增强蛋白质的活性（通过2,4-二取代喹啉衍生物与A3AR的结合）来实现治疗。当用于增强活性时，2,4-二取代喹啉衍生物可治疗的一些病症包括恶性肿瘤、免疫功能受损的疾病、高眼压或与高眼压相关的病症。本发明还提供了一种治疗可通过腺苷、A3AR激动剂或A3AR拮抗剂治疗的病症的方法，利用定义的2,4-二取代喹啉衍生物（们），以及包含该衍生物的药物组合物和包含该衍生物及使用说明的工具箱。一个具体的2,4-二取代喹啉衍生物包括N-2-[(3,4-二氯苯基)氨基]喹啉-4-基}环己烷羧酰胺。在一个实施例中，根据本发明，2,4-二取代喹啉衍生物以适合口服的形式制剂。