2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline | 149876-18-6

• 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: 2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
• 英文别名: 2-ethyl-1-(2-methylpropyl)imidazo[4,5-c]quinoline
• CAS: 149876-18-6
• 化学式: C₁₆H₁₉N₃
• 分子量: 253.347
• InChiKey: DPOUFQSXHHFUKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 在 过氧乙酸 、 ammonium hydroxide 、 对甲苯磺酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-ethyl-1-isobutyl-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
• 作为产物：
  描述：

  3-硝基-4-羟基喹啉 在 platinum on activated charcoal 氯化亚砜 、 氢气 、 magnesium sulfate 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.25h， 生成 2-ethyl-1-(2-methylpropyl)-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

• 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines
  申请人：Minnesota Mining and Manufacturing Company

  公开号：US05266575A1

  公开（公告）日：1993-11-30

  2-Ethyl 1H-imidazo[4,5-c]quinolin-4-amines, which are active as immunomodulators and antiviral agents, and intermediates in the preparation of such compounds, pharmaceutical compositions and pharmacological methods of use.

  2-乙基1H-咪唑[4,5-c]喹啉-4-胺具有免疫调节和抗病毒活性，是制备这类化合物、药物组合物和药理使用方法的中间体。
• [EN] ANTIVIRAL 2-ETHYL-1H-IMIDAZO(4,5-C)QUINOLIN-4-AMINES
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：WO1993009119A1

  公开（公告）日：1993-05-13

  (EN) 2-Ethyl 1H-imidazo[4,5-c]quinolin-4-amines of formula (I), active as immunomodulators and antiviral agents. Also, intermediates of formulae (II, III) in the preparation of such compounds, pharmaceutical compositions, and pharmacological methods of use.(FR) L'invention se rapporte aux amines 2-éthyl-1H-imidazo(4,5-c)quinoline-4 de la formule (I), efficaces comme agents immunomodulateurs et antiviraux. L'invention se rapporte également aux intermédiaires des formules (II et III) dans la préparation de tels composés, compositions pharmaceutiques et procédés d'utilisation pharmacologiques.

  (EN) 2-乙基1H-咪唑酰胺-4-位的quinolin-4-胺，化学式为(I)，作用于免疫调节剂和抗病毒药物。此外，还包括形态为(II、III)的中间体，在合成此类化合物中的辅助作用，药用配方，以及与药物治疗相关的药理方法. (FR) 发明涉及2-乙基-1H-Imidazo(4,5-c)quinoline-4号化学式为(I)的胺，具有免疫调节剂和抗病毒活性。在发明还涉及(II和III)中形态的中间体，在合成此类化合物中的辅助作用，药用配方，以及药物治疗的方法。
• ANTIVIRAL 2-ETHYL-1H-IMIDAZO(4,5-C)QUINOLIN-4-AMINES
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0641342A1

  公开（公告）日：1995-03-08
• US5266575A
  申请人：——

  公开号：US5266575A

  公开（公告）日：1993-11-30
• 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.