6-甲氧基-2-氨基喹啉 | 119990-33-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 6-甲氧基-2-氨基喹啉
• 英文名称: 2-amino-6-methoxy quinoline
• 英文别名: 6-methoxyquinolin-2-amine
• CAS: 119990-33-9
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: IADRCPCBGGCJKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-甲氧基-2-氨基喹啉 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.5h， 生成 7-methoxy-imidazo[1,2-a]quinoline-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009
• 作为产物：
  描述：

  N-(tert-butyl)-6-methoxyquinolin-2-amine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 6-甲氧基-2-氨基喹啉
  参考文献：
  名称：

  A General and Efficient 2-Amination of Pyridines and Quinolines

  摘要：

  Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.

  DOI：

  10.1021/jo070189y

文献信息

• Quinoline derivatives as antibacterials
  申请人：——

  公开号：US20040053928A1

  公开（公告）日：2004-03-18

  Aminopiperidine derivatives and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly in man.

  氨氧哌啶衍生物及其药用可接受的衍生物，用于治疗哺乳动物，特别是人类的细菌感染。
• TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE
  申请人：Hutchinson John Howard

  公开号：US20070173508A1

  公开（公告）日：2007-07-26

  Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of 5-lipoxygenase (5-LO). Also described herein are methods of using such 5-LO inhibitors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions, diseases, or disorders.

  本文描述了含有这些化合物的化合物和药物组合物，这些化合物抑制5-脂氧合酶（5-LO）的活性。本文还描述了使用这种5-LO抑制剂的方法，单独或与其他化合物结合，用于治疗呼吸系统、心血管系统和其他依赖或介导白三烯的状况、疾病或紊乱。
• Synthesis and Antihypertensive Activity of N-(Alkyl/alkenyl/aryl)-N'-heterocyclic Ureas and Thioureas
  作者：Opa Vajragupta、Aungkana Pathomsakul、Chutima Matayatsuk、Lek Ruangreangyingyod、Yuvadee Wongkrajang、William O. Foye

  DOI：10.1021/js930295x

  日期：1996.3

  significant antihypertensive activity (p < 0.05). 1-n-Propyl-3-[2'-(6-methoxy)quinolyl]urea (9), showing 29.1% reduction in systolic blood pressure, was the most active compound in the series. Two other compounds producing a fall in systolic blood pressure of the same magnitude were 1-allyl-3-[2'-(6-methyl)quinolyl]thiourea (4) and 1-n-propyl-3-[(2'-pyridyl)methyl]urea (17). Compound 17 with rapid

  -吡啶基）甲基]脲（17）。具有快速起效的化合物17可使离体的兔股动脉和豚鼠心房显着松弛（p <0.01），但对心律没有影响。然而，这些都没有显示出比哌唑嗪（5 mg / kg）更高的效力。当杂环核为吡啶时，作用力，起效和作用持续时间得到改善。
• Comparative quantitative structure–activity study of radical scavengers
  作者：Opa Vajragupta、Preecha Boonchoong、Yuvadee Wongkrajang

  DOI：10.1016/s0968-0896(00)00195-4

  日期：2000.11

  structure-activity relationship (3-D-QSAR) studies were performed by 3-D pharmacophore generation (Apex-3-D) and CoMFA techniques. For Apex-3-D studies, two best models with high Q2 (0.94 and 0.97) were yielded. Structural properties contributing to the activity were not only lipophilic but also the optimum steric property and geometry of side-chain composition. For CoMFA studies, the sp3 C(+1) probe provided the

  对13个自由基清除剂（1-13）进行了经典和三维（3-D）QSAR分析，得出了两个经典模型，两个Apex-3-D模型和一个比较场分析（CoMFA）模型。预测交叉验证的r2（Q2）超过0.96的两个经典模型表明，该活性归因于电子COH和ELUMO，空间摩尔折射率（MR）和亲脂对数P。三维定量构效关系（3-D -QSAR）研究是通过3-D药效团生成（Apex-3-D）和CoMFA技术进行的。对于Apex-3-D研究，产生了两个具有较高Q2的最佳模型（0.94和0.97）。有助于该活性的结构性质不仅是亲脂的，而且是最佳的空间性质和侧链组成的几何形状。对于CoMFA研究，sp3 C（+1）探针提供了0的最佳Q2。79位，其空间和静电贡献分别为42.3和57.7％。用这些模型预测了推导中未包括的四种新化合物（14-17）的活性。尽管派生模型来自有限的数据，但统计关系是可预测的。实验IC50值与经典和
• Mild, General, and Regioselective Synthesis of 2-Aminopyridines from Pyridine N-Oxides via N-(2-Pyridyl)pyridinium Salts
  作者：Hui Xiong、Adam T. Hoye

  DOI：10.1055/s-0040-1719865

  日期：2022.3

  2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt followed by hydrolytic decomposition of the pyridinium moiety to furnish the 2-aminopyridine product. The method is compatible with a wide range of functional groups, is

  已经证明和研究了从吡啶N-氧化物通过其相应的N- (2-吡啶基)吡啶鎓盐合成 2-氨基吡啶。该反应序列的特征在于将N-氧化物高度区域选择性地转化为其吡啶鎓盐，然后将吡啶鎓部分水解分解以提供 2-氨基吡啶产物。该方法与广泛的官能团兼容，具有可扩展性，并且具有廉价试剂的特点。15 N-标记结果给出了与 Zincke 反应机制一致的产品。