3-nitro-N-phenylquinolin-4-amine | 99009-93-5

• 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: 3-nitro-N-phenylquinolin-4-amine
• 英文别名: (3-nitro-[4]quinolyl)-phenyl-amine；(3-Nitro-[4]chinolyl)-phenyl-amin；3-Nitro-N-phenyl-4-quinolinamine
• CAS: 99009-93-5
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: LMSFLDIVWGQKLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitro-N-phenylquinolin-4-amine 在 platinum on activated charcoal 氢气 、 magnesium sulfate 作用下， 以 乙酸乙酯 为溶剂， 生成
  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：

  Nitroacetaldehyd 在 potassium acetate 、 乙酸酐 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 3-nitro-N-phenylquinolin-4-amine
  参考文献：
  名称：

  Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from a quinoline scaffold

  摘要：

  基于含有喹唑啉基团的EGFR抑制剂，合成并评估了一系列含有喹啉骨架的三十四种化合物的EGFR激酶抑制和抗癌活性。

  DOI：

  10.1039/c6ra15118c

文献信息

• The Synthesis of Some 3-Nitro- and 3-Amino-4-dialkylaminoalkylaminoquinoline Derivatives
  作者：Alexander R. Surrey、Royal A. Cutler

  DOI：10.1021/ja01150a002

  日期：1951.6
• Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from a quinoline scaffold
  作者：Monika Chauhan、Gaurav Joshi、Harveen Kler、Archana Kashyap、Suyog M. Amrutkar、Praveen Sharma、Kiran D. Bhilare、Uttam Chand Banerjee、Sandeep Singh、Raj Kumar

  DOI：10.1039/c6ra15118c

  日期：——

  Based on the quinazoline bearing EGFR inhibitors, a series of thirty four compounds having a quinoline scaffold were synthesized and evaluated in vitro for EGFR kinase inhibitory and anticancer activities.

  基于含有喹唑啉基团的EGFR抑制剂，合成并评估了一系列含有喹啉骨架的三十四种化合物的EGFR激酶抑制和抗癌活性。
• 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.