1,2-dimethyl-1H-imidazo[4,5-c]quinolin-5-oxide | 99023-56-0

• 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: 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-5-oxide
• 英文别名: 1,2-dimethyl-5-oxidoimidazo[4,5-c]quinolin-5-ium
• CAS: 99023-56-0
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: HOOFQGLGAHDHQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-dimethyl-1H-imidazo[4,5-c]quinolin-5-oxide 在 乙酸酐 作用下， 生成 1,2-dimethyl-4-hydroxy-1H-imidazo[4,5-c]quinoline
  参考文献：
  名称：

  1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents

  摘要：

  1H-咪唑并[4,5-c]喹啉是支气管扩张剂。描述了使用这些化合物作为支气管扩张剂的药理学方法，含有这些化合物的药物组合物，以及用于制备这些化合物的合成中间体。

  公开号：

  US04698348A1
• 作为产物：
  描述：

  1,2-dimethyl-1H-imidazo[4,5-c]quinoline 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 生成 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-5-oxide
  参考文献：
  名称：

  New bronchodilators. 1. 1,5-Substituted 1H-imidazo[4,5-c]quinolin-4(5H)-ones

  摘要：

  A series of novel xanthine-based tricyclic heterocycles in 1H-imidazo[4,5-c]quinolin-4(5H)-ones was designed, synthesized, and tested as potential active bronchodilators. Inhibition of the Schulz-Dale (SD) reaction-induced contraction in trachea and inhibition of antigen inhalation-induced bronchospasm in passively sensitized guinea pigs served as primary in vitro and in vivo assays, respectively. Simultaneous measurement of acute lethal toxicity (minimum lethal dose; MLD, po) in mice allowed determination of a safety margin. The bronchodilatory activity of these heterocycles was considerably varied with the nature of substituents at the 5-position. The most active substituents at the 2- and 5-positions and on the aromatic ring were found to be hydrogen, n-butyl, and hydrogen, respectively. There was a bulk tolerance for lipophilic substituents at the 1-position. 5-Butyl-substituted compounds appeared to be less toxic than theophylline on the basis of MLD data. Thus 5-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4(5H)-one (10) (IC50 value of the SD assay = 0.25 muM, MLD > 300 mg/kg) was selected for further studies. Compound 10 (KF15570) reduced bronchoconstriction produced by antigen (Konzett-Rossler preparation in anesthetized guinea pigs, ED50 = 0.42 mg/kg, iv) more effectively than aminophylline (ethylenediamine salt of theophylline, ED50 = 7.8 mg/kg, iv) but had fewer side effects on the heart and CNS than theophylline. Compound 10 and its derivatives showed weak adenosine antagonism and phosphodiesterase (PDE) inhibition which could not account for their potent bronchodilation. Although their precise mechanism of action remains unclear, this series of novel tricyclic heterocycles represents a new class of bronchodilator.

  DOI：

  10.1021/jm00100a009

文献信息

• 1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents
  申请人：Riker Laboratories, Inc.

  公开号：US04698348A1

  公开（公告）日：1987-10-06

  1H-imidazo[4,5-c]quinoline which are bronchodilators. Pharmacological methods of using the compounds as bronchodilators, pharmaceutical compositions containing the compounds, and synthetic intermediate for preparing the compounds are also described.

  1H-咪唑并[4,5-c]喹啉是支气管扩张剂。描述了使用这些化合物作为支气管扩张剂的药理学方法，含有这些化合物的药物组合物，以及用于制备这些化合物的合成中间体。
• Substituted Fused [1,2]Imidazo[4,5-C] Ring Compounds and Methods
  申请人：Rice Michael J.

  公开号：US20090005371A1

  公开（公告）日：2009-01-01

  Fused [1,2]imidazo[4,5-c] ring compounds, e.g., fused [1,2]imidazo[4,5-c]quinolines and [1,2]imidazo[4,5-c]naphthyridines, with a substituent, e.g., a substituted alkoxy substituent, at the 6, 7, 8, or 9-position, pharmaceutical compositions containing the compounds, intermediates, methods of making and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明涉及在6、7、8或9位具有取代的烷氧基取代基的融合[1,2]咪唑[4,5-c]环化合物，例如融合[1,2]咪唑[4,5-c]喹啉和[1,2]咪唑[4,5-c]萘啉，以及含有这些化合物的制药组合物、中间体、制备方法和用作免疫调节剂的方法，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。
• US4689338A
  申请人：——

  公开号：US4689338A

  公开（公告）日：1987-08-25
• US4698348A
  申请人：——

  公开号：US4698348A

  公开（公告）日：1987-10-06
• US8093390B2
  申请人：——

  公开号：US8093390B2

  公开（公告）日：2012-01-10