N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine | 144660-62-8

• 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: N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
• 英文别名: Benzamide, N-[1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-yl]-；N-[1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-yl]benzamide
• CAS: 144660-62-8
• 化学式: C₂₁H₂₀N₄O
• 分子量: 344.416
• InChiKey: TZTHLAVJQIFKRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  193-196 °C(Solv: ethanol (64-17-5))
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 羟丙基甲基纤维素邻苯二甲酸酯
  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
• 作为产物：
  描述：

  4-异丁胺基-3-硝基喹啉 在 platinum on activated charcoal 过氧乙酸 、 氢气 、 magnesium sulfate 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 60.0 ℃ 、365.42 kPa 条件下， 反应 3.75h， 生成 N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine
  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

• Imidazo[4,5-c]quinolin-4-amines and processes for their preparation
  申请人：Minnesota Mining and Manufacturing Company

  公开号：US05175296A1

  公开（公告）日：1992-12-29

  A process and intermediates for preparing 1-substituted-1H-imidazo[4,5-c]quinolin-4-amines. The process involves reacting a 1-substituted-1H-imidazo[4,5-c]quinoline-5N-oxide with an isocyanate and hydrolysing the product thereof. Also, a process for preparing the intermediates is disclosed.

  制备1-取代-1H-咪唑[4,5-c]喹啉-4-胺的过程和中间体。该过程涉及将1-取代-1H-咪唑[4,5-c]喹啉-5N-氧化物与异氰酸酯反应，并水解其产物。此外，还公开了制备中间体的过程。
• PROCESS FOR IMIDAZO [4,5-c]QUINOLIN-4-AMINES
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0575549B1

  公开（公告）日：1996-09-11
• US5175296A
  申请人：——

  公开号：US5175296A

  公开（公告）日：1992-12-29
• [EN] PROCESS FOR IMIDAZO[4,5-c]QUINOLIN-4-AMINES
  申请人：——

  公开号：WO1992015581A1

  公开（公告）日：1992-09-17

  [FR] Procédé et intermédiaire servant à la préparation de 1H-imidazo[4,5-c]quinolin-4-amines substituées en position 1. Le procédé consiste à faire réagir un 5N-oxyde de 1H-imidazo[4,5-c]quinoline avec un isocyanate et à hydroliser le produit de la réaction. L'invention concerne également un procédé de préparation des intermédiaires.
  [EN] A process and intermediates for preparing 1-substituted-1H-imidazo[4,5-c]quinolin-4-amines. The process involves reacting a 1-substituted-1H-imidazo[4,5-c]quinoline-5N-oxide with an isocyanate and hydrolysing the product thereof. Also, a process for preparing the intermediates is disclosed.
• 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.