咪喹莫特相关物质D | 853792-81-1

• 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
• 中文名称: 咪喹莫特相关物质D
• 中文别名: 1-丙基-1H-咪唑并[4,5-C]喹啉-4-胺
• 英文名称: 1-Propyl-1H-imidazo[4,5-c]quinolin-4-ylamine
• 英文别名: 1-Propyl-1H-imidazo[4,5-c]quinolin-4-amine；1-propylimidazo[4,5-c]quinolin-4-amine
• CAS: 853792-81-1
• 化学式: C₁₃H₁₄N₄
• 分子量: 226.281
• InChiKey: OWBUYSQOBLYANO-UHFFFAOYSA-N

物化性质

• 熔点：
  288-290℃
• 沸点：
  457.4±48.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  3-硝基-4-羟基喹啉 在 platinum on activated charcoal 过氧乙酸 、 ammonium hydroxide 、 氯化亚砜 、 氢气 、 magnesium sulfate 、 三乙胺 、 N,N-二甲基甲酰胺 、 对甲苯磺酰氯 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0~60.0 ℃ 、344.74 kPa 条件下， 反应 3.0h， 生成 咪喹莫特相关物质D
  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

• US8357374B2
  申请人：——

  公开号：US8357374B2

  公开（公告）日：2013-01-22
• [EN] PHARMACEUTICAL COMPOSITIONS COMPRISING IMIDAZOQUINOLIN(AMINES) AND DERIVATIVES THEREOF SUITABLE FOR LOCAL ADMINISTRATION<br/>[FR] COMPOSITIONS PHARMACEUTIQUES COMPRENANT DES IMIDAZOQUINOLIN(AMINES) ET DES DÉRIVÉS DE CELLES-CI APPROPRIÉES POUR UNE ADMINISTRATION LOCALE
  申请人：TELORMEDIX SA

  公开号：WO2010089128A2

  公开（公告）日：2010-08-12

  The present invention relates in general to the field of modulators of the innate immune system, particularly to pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof, preferably suitable for local administration, such as, intravesical administration. In addition, the present invention concerns the use of imidazoquinolin(amines) and derivatives thereof for intravesical treatment of bladder diseases, such as, for example, bladder cancer and cystitis. The present invention furthermore comprises methods of treatment for these diseases as well as methods of administration of the inventive pharmaceutical compositions.
• 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.