4-chloro-1-(1,1-dimethylethyl)-1H-imidazo[4,5-c]quinoline | 132521-60-9

• 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-(1,1-dimethylethyl)-1H-imidazo[4,5-c]quinoline
• 英文别名: 1-Tert-butyl-4-chloroimidazo[4,5-c]quinoline
• CAS: 132521-60-9
• 化学式: C₁₄H₁₄ClN₃
• 分子量: 259.738
• InChiKey: NNFXNCYEEJCUSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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-(1,1-dimethylethyl)-1H-imidazo[4,5-c]quinoline 在 盐酸 、 氨 作用下， 反应 0.5h， 生成 3H-咪唑并[4,5-c]喹啉-4-氨
  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：

  tert-Butyl-(2-chloro-3-nitro-quinolin-4-yl)-amine 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-(1,1-dimethylethyl)-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)Quinolin-4-amines as antivirals
  申请人：RIKER LABORATORIES, INC.

  公开号：EP0385630A2

  公开（公告）日：1990-09-05

  Novel 1H-imidazo[4,5-c]quinolin-4-amines of formula are disclosed. The compounds function as antiviral agents and they are potential synthetic intermediates in the preparation of known antiviral agents and labeled known antiviral agents. Processes for the preparation of the compounds, methods for their antiviral use, and methods of inducing interferon biosynthesis, are also described.

  新颖的 1H-咪唑并[4,5-c]喹啉-4-胺式 公开。这些化合物具有抗病毒剂的功能，是制备已知抗病毒剂和标记已知抗病毒剂的潜在合成中间体。此外，还描述了制备这些化合物的工艺、使用这些化合物抗病毒的方法以及诱导干扰素生物合成的方法。
• Olefinic 1H-imidazo [4,5-c]quinolin-4-amines
  申请人：RIKER LABORATORIES, INC.

  公开号：EP0389302B1

  公开（公告）日：1994-08-31
• US5037986A
  申请人：——

  公开号：US5037986A

  公开（公告）日：1991-08-06
• US5756747A
  申请人：——

  公开号：US5756747A

  公开（公告）日：1998-05-26
• 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.