8-chloro-1-methyl-1H-imidazo[4,5-c]quinoline | 133306-55-5

• 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: 8-chloro-1-methyl-1H-imidazo[4,5-c]quinoline
• 英文别名: 8-chloro-1-methylimidazo[4,5-c]quinoline
• CAS: 133306-55-5
• 化学式: C₁₁H₈ClN₃
• 分子量: 217.658
• InChiKey: CNDRNYWLWQVVKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-chloro-1-methyl-1H-imidazo[4,5-c]quinoline 在 双氧水 、 溶剂黄146 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4,8-dichloro-1-methyl-1H-imidazo[4,5-c]quinoline
  参考文献：
  名称：

  [EN] HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE
  [FR] INHIBITEURS HÉTÉROCYCLIQUES DE RÉCEPTEURS DE L'HISTAMINE DESTINÉS AU TRAITEMENT DE MALADIE

  摘要：

  公开号：

  WO2011112731A3
• 作为产物：
  描述：

  4,6-二氯-3-硝基喹啉 在 盐酸 、 sodium dithionite 、 水 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 2.5h， 生成 8-chloro-1-methyl-1H-imidazo[4,5-c]quinoline
  参考文献：
  名称：

  [EN] HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE
  [FR] INHIBITEURS HÉTÉROCYCLIQUES DE RÉCEPTEURS DE L'HISTAMINE DESTINÉS AU TRAITEMENT DE MALADIE

  摘要：

  公开号：

  WO2011112731A3

文献信息

• HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE
  申请人：Borchardt Allen J.

  公开号：US20100120741A1

  公开（公告）日：2010-05-13

  The present invention relates to compounds and methods which may be useful as inhibitors of H 1 R and/or H 4 R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

  本发明涉及化合物和方法，这些化合物和方法可能用作H1R和/或H4R的抑制剂，用于治疗或预防炎症性、自身免疫性、过敏性和眼部疾病。
• Imidazoquinolone derivatives
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US04994468A1

  公开（公告）日：1991-02-19

  Novel imidazoquinolone derivative represented by the formula (I); ##STR1## wherein R.sup.1 represents hydrogen, alkyl, cycloalkyl, alkenyl aralkyl, aralkenyl or substituted or unsubstituted aryl; X represents nitrogen or ##STR2## where R.sup.2 is hydrogen, hydroxyl, alkyl, cycloalkyl, alkenyl, aralkyl, aralkenyl, substituted or unsubstituted aryl, thiol, halogen, substituted or unsubstituted aromatic heterocyclic group, or --(CH.sub.2).sub.m CO.sub.2 R.sup.6 where R.sup.6 is hydrogen or lower alkyl and m is an integer of 0 to 3; Y represents oxygen or sulfur; R.sup.3 represents alkyl, cycloalkyl, alkoxyalkly, alkenyl, aralkyl, aralkenyl, --(CH.sub.2).sub.n -- Het where Het is substituted or unsubstituted aromatic heterocyclic group and n is an integer of 1 to 3 or --(CH.sub.2).sub.n CO.sub.2 R.sup.6a where n has the same meaning as defined above and R.sup.6a has the same meaning as defined as to R.sup.6 ; each of R.sup.4 and R.sup.5 independently represents hydrogen, lower alkyl, trifluoromethyl, cycloalkyl, halogen, hydroxyl, lower alkoxyl, lower alkylthio, nitro, amino, lower alkylamino, lower alkanoylamino, aroylamino, lower alkanoyl or aroyl; and a pharmaceutically acceptable salt thereof. The Compound (I) and a pharmaceutically acceptable salt thereof show bronchodilatory and antiallergic activities, and are useful for treating respiratory disorders such as bronchial asthma.

  新型咪唑喹酮衍生物的化学式（I）所代表的是：其中R.sup.1代表氢、烷基、环烷基、烯基芳基、烯基芳基或取代或未取代芳基；X代表氮或##STR2##其中R.sup.2为氢、羟基、烷基、环烷基、烯基、芳基、硫醇、卤素、取代或未取代芳香杂环基，或--（CH.sub.2）.sub.m CO.sub.2 R.sup.6，其中R.sup.6为氢或较低烷基，m为0到3的整数；Y代表氧或硫；R.sup.3代表烷基、环烷基、烷氧基烷基、烯基、芳基、烯基芳基、--（CH.sub.2）.sub.n -- Het，其中Het为取代或未取代芳香杂环基，n为1到3的整数，或--（CH.sub.2）.sub.n CO.sub.2 R.sup.6a，其中n具有上述定义的相同含义，R.sup.6a具有与R.sup.6相同的定义；R.sup.4和R.sup.5中的每一个独立地代表氢、较低烷基、三氟甲基、环烷基、卤素、羟基、较低烷氧基、较低烷基硫基、硝基、氨基、较低烷基氨基、较低烷酰胺基、芳酰胺基、较低烷酰基或芳酰基；以及其药学上可接受的盐。化合物（I）及其药学上可接受的盐具有支气管扩张和抗过敏活性，并且可用于治疗支气管哮喘等呼吸系统疾病。
• New bronchodilators. 1. 1,5-Substituted 1H-imidazo[4,5-c]quinolin-4(5H)-ones
  作者：Fumio Suzuki、Takeshi Kuroda、Yoshisuke Nakasato、Haruhiko Manabe、Kenji Ohmori、Shigeto Kitamura、Shunji Ichikawa、Tetsuji Ohno

  DOI：10.1021/jm00100a009

  日期：1992.10

  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.
• US4994468A
  申请人：——

  公开号：US4994468A

  公开（公告）日：1991-02-19
• [EN] HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS HÉTÉROCYLIQUES DES RÉCEPTEURS DE L'HISTAMINE DESTINÉS AU TRAITEMENT D'UNE MALADIE
  申请人：KALYPSYS INC

  公开号：WO2010030785A2

  公开（公告）日：2010-03-18

  The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.