1-Isopropyl-1H-imidazo[4,5-c]quinolin-4-ylamine | 853792-82-2

• 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-Isopropyl-1H-imidazo[4,5-c]quinolin-4-ylamine
• 英文别名: 1-(1-Methylethyl)-1H-imidazo[4,5-c]quinolin-4-amine；1-propan-2-ylimidazo[4,5-c]quinolin-4-amine
• CAS: 853792-82-2
• 化学式: C₁₃H₁₄N₄
• 分子量: 226.281
• InChiKey: MZHCMKLGOQGXGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基喹啉 在 platinum on activated charcoal 过氧乙酸 、 氯化亚砜 、 氨 、 氢气 、 硝酸 、 magnesium sulfate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 丙酸 、 乙酸乙酯 为溶剂， 60.0~150.0 ℃ 、344.74 kPa 条件下， 反应 3.25h， 生成 1-Isopropyl-1H-imidazo[4,5-c]quinolin-4-ylamine
  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

• Imiquimod formulation
  申请人：Winckle Gareth

  公开号：US20090182004A1

  公开（公告）日：2009-07-16

  Solutions of members of the imidazoquinoline family of drugs, such as imiquimod or an analog thereof, are made by combining the drug in a solvent system containing one or more non-aqueous solvents and a hydrogen bond forming compound, wherein the solvent system contains a low level of water.
• [EN] IMIQUIMOD FORMULATION<br/>[FR] FORMULATION D'IMIQUIMOD
  申请人：DOW PHARMACEUTICAL SCIENCES

  公开号：WO2009091541A1

  公开（公告）日：2009-07-23

  Solutions of members of the imidazoquinoline family of drugs, such as imiquimod or an analog thereof, are made by combining the drug in a solvent system containing one or more non-aqueous solvents and a hydrogen bond forming compound, wherein the solvent system contains a low level of water.
• Synthesis and Structure−Activity-Relationships of 1<i>H</i>-Imidazo[4,5-<i>c</i>]quinolines That Induce Interferon Production
  作者：John F. Gerster、Kyle J. Lindstrom、Richard L. Miller、Mark A. Tomai、Woubalem Birmachu、Shannon N. Bomersine、Shiela J. Gibson、Linda M. Imbertson、Joel R. Jacobson、Roy T. Knafla、Peter V. Maye、Nickolas Nikolaides、Folakemi Y. Oneyemi、Gwen J. Parkhurst、Sharon E. Pecore、Michael J. Reiter、Lisa S. Scribner、Tracy L. Testerman、Natalie J. Thompson、Tammy L. Wagner、Charles E. Weeks、Jean-Denis Andre、Daniel Lagain、Yvon Bastard、Michel Lupu

  DOI：10.1021/jm049211v

  日期：2005.5.1

  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.