4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]-quinoline | 129655-65-8

• 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: 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]-quinoline
• 英文别名: 4-Chloro-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol；4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline；1-(4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol；4-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol；1-(4-chloroimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
• CAS: 129655-65-8
• 化学式: C₁₄H₁₄ClN₃O
• 分子量: 275.738
• InChiKey: DHXCFDWZILVFEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]-quinoline 在 氨 作用下， 以 甲醇 为溶剂， 生成 1-(4-氨基咪唑并[4,5-c]喹啉-1-基)-2-甲基丙烷-2-醇
  参考文献：
  名称：

  1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use

  摘要：

  1H-咪唑并[4,5-c]喹啉-4-胺是抗病毒药物。还描述了使用这些化合物的药理学方法以及含有这些化合物的药物组合物。

  公开号：

  US04689338A1
• 作为产物：
  描述：

  1-[(2-氯-3-硝基-4-喹啉基)氨基]-2-甲基-2-丙醇 在 platinum on activated charcoal 氢气 、 magnesium sulfate 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 生成 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]-quinoline
  参考文献：
  名称：

  Synthesis and Structure−Activity-Relationships of 1H-Imidazo[4,5-c]quinolines That Induce Interferon Production

  摘要：

  1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

  DOI：

  10.1021/jm049211v

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。
• Sulfone substituted imidazo ring ethers
  申请人：Radmer R. Matthew

  公开号：US20070155767A1

  公开（公告）日：2007-07-05

  Imidazo ring compounds (e.g., imidazoquinolines, 6,7,8,9-tetrahydroimidazoquinolines, imidazonaphthyridines, and 6,7,8,9-tetrahydroimidazonaphthyridines) with a sulfide-, sulfinyl-, or sulfonyl-containing ether substituent at the 1-position, pharmaceutical compositions containing the compounds, intermediates, methods of making the compounds, 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.

  咪唑环化合物（例如咪唑喹啉，6,7,8,9-四氢咪唑喹啉，咪唑萘啉和6,7,8,9-四氢咪唑萘啉）在1-位置具有含硫醚，亚砜基或磺酰基的醚取代基，含有这些化合物的药物组合物，中间体，制备这些化合物的方法，以及将这些化合物用作免疫调节剂的方法，用于诱导动物中的细胞因子生物合成以及治疗包括病毒性和肿瘤性疾病在内的疾病。
• 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use
  申请人：Riker Laboratories, Inc.

  公开号：US04689338A1

  公开（公告）日：1987-08-25

  1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described.

  1H-咪唑并[4,5-c]喹啉-4-胺是抗病毒药物。还描述了使用这些化合物的药理学方法以及含有这些化合物的药物组合物。
• Process for reparing imidazoquinolinamines
  申请人：Minnesota Mining and Manufacturing Company

  公开号：US05741908A1

  公开（公告）日：1998-04-21

  A process for preparing 1H-imidazo\x9b4,5-c!quinolin-4-amines is disclosed. The process involves reacting a 6H-imidazo\x9b4,5-c!tetrazolo\x9b1,5-a!quinoline with triphenylphosphine and hydrolyzing the product thereof.

  公开了一种制备1H-咪唑[4,5-c]喹啉-4-胺的方法。该方法涉及将6H-咪唑[4,5-c]四唑[1,5-a]喹啉与三苯基膦反应，然后水解产物。
• 3-Amino or 3-nitro quinoline compounds which are intermediates in
  申请人：Riker Laboratories, Inc.

  公开号：US04988815A1

  公开（公告）日：1991-01-29

  A process for the preparation of 1-substituted, 4-substituted-1H-imidazo[4,5-c]quinolines, intermediates in the preparation of such compounds, and processes for the preparation of such intermediates.

  一种制备1-取代基，4-取代基-1H-咪唑并[4,5-c]喹啉的方法，用于制备这类化合物的中间体，以及制备这类中间体的方法。