N,2-Dicyclopentyl-1H-imidazo[4,5-c]quinolin-4-amine | 132207-00-2

• 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: N,2-Dicyclopentyl-1H-imidazo[4,5-c]quinolin-4-amine
• 英文别名: N,2-dicyclopentyl-3H-imidazo[4,5-c]quinolin-4-amine
• CAS: 132207-00-2
• 化学式: C₂₀H₂₄N₄
• 分子量: 320.437
• InChiKey: VVEHKPZLRKEVHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基-3-硝基喹啉 在 palladium on activated charcoal 氢气 、 sodium carbonate 、 间氯过氧苯甲酸 、 三氯氧磷 、 原甲酸三甲酯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 25.0~105.0 ℃ 、101.33 kPa 条件下， 反应 8.67h， 生成 N,2-Dicyclopentyl-1H-imidazo[4,5-c]quinolin-4-amine
  参考文献：
  名称：

  1H-Imidazo[4,5-c]quinolin-4-amines: novel non-xanthine adenosine antagonists

  摘要：

  On the basis of a model we recently developed for the antagonist binding site of the adenosine A1 receptor (J. Med. Chem. 1990, 33, 1708-1713), it was predicted that H-1-imidazo[4,5-c]quinolin-4-amines would be antagonists of the A1 receptor. Furthermore, it was expected that certain hydrophobic substitutions at the 2- and 4-positions would enhance affinity. Here, we report on the synthesis and the adenosine A1 and A2 recpetor affinity of substituted H-1-imidazo[4,5-c]quinolin-4-amines. Some of these compounds have nanomolar affinity for the A1 receptor. The structure-activity relationships (SAR) of these compounds are discussed in relation to SAR for other adenosine receptor ligands. The H-1-imidazo[4,5-c]quinolin-4-amines constitute a novel class of non-xanthine adenosine antagonists.

  DOI：

  10.1021/jm00107a046

文献信息

• VAN, GALEN PHILIP J. M..;NISSEN, PETER;VAN, WIJNGAARDEN INEKE;JZERMAN, AD+, J. MED. CHEM., 34,(1991) N, C. 1202-1206
  作者：VAN, GALEN PHILIP J. M..、NISSEN, PETER、VAN, WIJNGAARDEN INEKE、JZERMAN, AD+

  DOI：——

  日期：——
• 1H-Imidazo[4,5-c]quinolin-4-amines: novel non-xanthine adenosine antagonists
  作者：Philip J. M. Van Galen、Peter Nissen、Ineke Van Wijngaarden、Adriaan P. Ijzerman、Willem Soudijn

  DOI：10.1021/jm00107a046

  日期：1991.3

  On the basis of a model we recently developed for the antagonist binding site of the adenosine A1 receptor (J. Med. Chem. 1990, 33, 1708-1713), it was predicted that H-1-imidazo[4,5-c]quinolin-4-amines would be antagonists of the A1 receptor. Furthermore, it was expected that certain hydrophobic substitutions at the 2- and 4-positions would enhance affinity. Here, we report on the synthesis and the adenosine A1 and A2 recpetor affinity of substituted H-1-imidazo[4,5-c]quinolin-4-amines. Some of these compounds have nanomolar affinity for the A1 receptor. The structure-activity relationships (SAR) of these compounds are discussed in relation to SAR for other adenosine receptor ligands. The H-1-imidazo[4,5-c]quinolin-4-amines constitute a novel class of non-xanthine adenosine antagonists.