1-hexadecyl-1H-imidazo[4,5-c]quinoline

• 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: 1-hexadecyl-1H-imidazo[4,5-c]quinoline
• 英文别名: 1-Hexadecylimidazo[4,5-c]quinoline；1-hexadecylimidazo[4,5-c]quinoline
• 化学式: C₂₆H₃₉N₃
• 分子量: 393.616
• InChiKey: TVEUKUZUDMCZMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-hexadecyl-1H-imidazo[4,5-c]quinoline 在 过氧乙酸 作用下， 以 乙醇 为溶剂， 生成 1-Hexadecyl-1H-imidazo[4,5-c]quinoline 5-oxide
  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 3.0h， 生成 1-hexadecyl-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

• AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC, AND ANTICANCER ACTIVITY
  申请人：WELLSTAT THERAPEUTICS CORPORATION

  公开号：US20150361077A1

  公开（公告）日：2015-12-17

  Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

  本文描述了对炎症、真菌、单细胞寄生微生物和癌症具有活性的胺化合物。这些化合物包含一个单环、双环或三环芳香环，其中含有一个、两个或三个环氮原子。
• Amine compounds having anti-inflammatory, antifungal, antiparasitic, and anticancer activity
  申请人：Wellstat Therapeutics Corporation

  公开号：US10030015B2

  公开（公告）日：2018-07-24

  Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

  本文描述了具有抗炎、抗真菌、抗单细胞寄生微生物和抗癌活性的胺化合物。这些化合物含有单环、双环或三环芳香环，环上有一个、两个或三个氮原子。
• Aminoquinazoline compounds having anti-inflammatory, antifungal, antiparasitic, and anticancer activity
  申请人：Wellstat Therapeutics Corporation

  公开号：US10934284B2

  公开（公告）日：2021-03-02

  Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

  本文描述了具有抗炎、抗真菌、抗单细胞寄生微生物和抗癌活性的胺化合物。这些化合物含有单环、双环或三环芳香环，环上有一个、两个或三个氮原子。
• AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY
  申请人：Wellstat Therapeutics Corporation

  公开号：EP2950649B1

  公开（公告）日：2020-03-04
• AMINOQUINOLINE COMPOUNDS HAVING ANTICANCER ACTIVITY
  申请人：Wellstat Therapeutics Corporation

  公开号：US20180298000A1

  公开（公告）日：2018-10-18

  Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.