4-hydroxy-8-methyl-3-nitroquinolin-2-(1H)-one | 54675-48-8

• 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: 4-hydroxy-8-methyl-3-nitroquinolin-2-(1H)-one
• 英文别名: 4-hydroxy-8-methyl-3-nitro-1H-quinolin-2-one；4-hydroxy-8-methyl-3-nitrocarbostyril；4-hydroxy-8-methyl-3-nitro-1H-quinolin-2-one
• CAS: 54675-48-8
• 化学式: C₁₀H₈N₂O₄
• 分子量: 220.185
• InChiKey: QKVRYPMJNCQYGL-UHFFFAOYSA-N

物化性质

• 沸点：
  406.4±45.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-8-methyl-3-nitroquinolin-2-(1H)-one 在 platinum on activated charcoal 苯膦酰二氯 、 氨 、 氢气 、 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 135.0~150.0 ℃ 、344.74 kPa 条件下， 反应 3.0h， 生成 1-Isobutyl-6-methyl-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
• 作为产物：
  描述：

  4-羟基-8-甲基-2-喹啉酮 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 生成 4-hydroxy-8-methyl-3-nitroquinolin-2-(1H)-one
  参考文献：
  名称：

  Anti-allergenic carbostyril derivatives

  摘要：

  一类4-羟基-3-硝基耳波斯蒂尔衍生物在抑制特定类型的抗原抗体反应中很有用。

  公开号：

  US03962445A1

文献信息

• 4-Hydroxy-3-nitro-carbostyril compounds
  申请人：Beecham Group Limited

  公开号：US04065457A1

  公开（公告）日：1977-12-27

  A class of 4-hydroxy-3-nitrocarbostyril derivatives are useful in the inhibition of certain types of antigen antibody reactions.

  一类4-羟基-3-硝基喹啉衍生物可用于抑制某些类型的抗原抗体反应。
• EP0688319A4
  申请人：——

  公开号：EP0688319A4

  公开（公告）日：1996-02-28
• 4-HYDROXY-3-NITRO-1,2-DIHYDROQUINOLIN-2-ONES AND THE USE THEREOF AS EXCITATORY AMINO ACID AND GLYCINE RECEPTOR ANTAGONISTS
  申请人：STATE OF OREGON, acting by and through THE OREGON STATE BOARD OF HIGHER EDUCATION, acting for and on behalf of

  公开号：EP0688319A1

  公开（公告）日：1995-12-27
• US4192876A
  申请人：——

  公开号：US4192876A

  公开（公告）日：1980-03-11
• US5622965A
  申请人：——

  公开号：US5622965A

  公开（公告）日：1997-04-22