1-benzyl-4-chloro-1H-imidazo[4,5-c]quinoline | 99010-78-3

• 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-benzyl-4-chloro-1H-imidazo[4,5-c]quinoline
• 英文别名: 1-benzyl-4-chloroimidazo[4,5-c]quinoline
• CAS: 99010-78-3
• 化学式: C₁₇H₁₂ClN₃
• 分子量: 293.755
• InChiKey: GYQPLQGFPJBAJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1-benzyl-4-chloro-1H-imidazo[4,5-c]quinoline 在 氨 作用下， 生成 1-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine
  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：

  N⁴-benzylquinoline-3,4-diamine 在 过氧乙酸 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-benzyl-4-chloro-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。
• 1H-Imidazo[4,5-c]quinolines and 1H-imidazo[4,5-c]quinolin-4-amines
  申请人：RIKER LABORATORIES, INC.

  公开号：EP0145340B1

  公开（公告）日：1990-01-24
• Quinoline intermediates for the synthesis of 1H-imidazo[4,5-c]quinolines and 1H-imidazo[4,5-c]quinolin-4-amimes
  申请人：RIKER LABORATORIES, INC.

  公开号：EP0310950B1

  公开（公告）日：1993-01-13
• GERSTER, JOHN F.
  作者：GERSTER, JOHN F.

  DOI：——

  日期：——
• TOLL-LIKE RECEPTOR-7 AND -8 MODULATORY 1H IMIDAZOQUINOLINE DERIVED COMPOUNDS
  申请人：The University of Kansas

  公开号：US20180134701A1

  公开（公告）日：2018-05-17

  The present disclosure provides novel imidazoquinoline derived compounds, derivatives thereof, analogues thereof, and pharmaceutically acceptable salts thereof, and methods of making and using such compounds. The present disclosure also provides TLR7 agonists and TLR7/TLR8 dual agonists, probes, tissue-specific molecules, adjuvants, immunogenic compositions, therapeutic compositions, and self-adjuvanting vaccines including the imidazoquinoline derived compounds, derivatives thereof, analogues thereof, and pharmaceutically acceptable salts thereof. Derivatives of the imidazoquinoline derived compounds also include dendrimers and dimers of the imidazoquinoline derived compounds, and methods of making and using the dendrimeric and dimeric imidazoquinoline derived compounds. The present disclosure also provides dual TLR2/TLR7 hybrid agonists that include imidazoquinoline derived compounds of the present disclosure.