4-chloro-1-methyl-1H-imidazo[4,5-c]quinoline | 99010-75-0

• 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: 4-chloro-1-methyl-1H-imidazo[4,5-c]quinoline
• 英文别名: 4-chloro-1-methylimidazo[4,5-c]quinoline
• CAS: 99010-75-0
• 化学式: C₁₁H₈ClN₃
• 分子量: 217.658
• InChiKey: RYXSAHOTOCVZEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：

  4-chloro-1-methyl-1H-imidazo[4,5-c]quinoline 在 sodium methylate 作用下， 生成 1-methyl-4-methoxy-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：

  4-(methylamino)-3-nitroquinoline 在 platinum on activated charcoal 过氧乙酸 、 氢气 、 magnesium sulfate 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 生成 4-chloro-1-methyl-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

• Novel [1,3]-migration of methyl group in imidazo[4,5-c]quinoline
  作者：Takeshi Kuroda、Fumio Suzuki

  DOI：10.1016/0040-4039(92)88131-n

  日期：1992.4

  In synthetic studies of imidazo[4,5-c]quinolin-4(5H)-one derivatives, which exhibit a potent antiasthmatic activity, an unusual rearrangement was observed, where the methyl group migrates from the N-1 to the N-3 position on the imidazole during the reaction of Chapman rearrangement of 1-methyl-4-phenoxy-1H-imidazo[4,5-c]quinoline 2.
• 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
• 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