7-methoxy-imidazo[1,2-a]quinoline-2-carboxylic acid | 68050-36-2

• 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: 7-methoxy-imidazo[1,2-a]quinoline-2-carboxylic acid
• 英文别名: 7-methoxyimidazo-[1,2-a]-quinoline-2-carboxylic acid；7-Methoxyimidazo<1,2-a>chinolin-2-carbonsaeure；7-methoxyimidazo[1,2-a]quinoline-2-carboxylic acid
• CAS: 68050-36-2
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: OEXFFPIXFHWFDK-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• Novel imidazoquinolines
  申请人：Roussel Uclaf

  公开号：US04279912A1

  公开（公告）日：1981-07-21

  Novel imidazoquinolines of the formula ##STR1## wherein X and Y are individually selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms, Z is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms optionally substituted with at least two hydroxyls or protected hydroxyls and ##STR2## n is an integer from 1 to 6 and R.sub.1 and R.sub.2 are individually alkyl of 1 to 5 carbon atoms and taken together with the nitrogen to which they are attached form a saturated heterocyclic ring containing 4 to 6 carbon atoms and optionally interrupted by another heteroatom which further heteroatom is optionally substituted with alkyl of 1 to 5 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof having antiallergic and bronchodilatory activity and their preparations.

  新型咪唑喹啉的化学式为##STR1##其中X和Y分别选自氢、卤素和1至5个碳原子的烷氧基组成的群，Z选自氢、1至5个碳原子的烷基，可选地被至少两个羟基或保护羟基取代，并且##STR2##n是1至6的整数，R.sub.1和R.sub.2分别是1至5个碳原子的烷基，并与它们连接的氮一起形成含有4至6个碳原子的饱和杂环环，可选地被另一个杂原子中断，该另一个杂原子可选地被1至5个碳原子的烷基取代，以及其无毒、药学上可接受的盐，具有抗过敏和支气管扩张活性以及它们的制备。
• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——
• US4279912A
  申请人：——

  公开号：US4279912A

  公开（公告）日：1981-07-21
• 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
  作者：Ian R. Ager、Alan C. Barnes、Geoffrey W. Danswan、Peter W. Hairsine、David P. Kay、Peter D. Kennewell、Saroop S. Matharu、Peter Miller、Peter Robson

  DOI：10.1021/jm00401a009

  日期：1988.6

  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.