8-氯-4-(3-{4-[2-(2,2,2-三氟-乙氧基)-苯基]-哌嗪-1-基}-丙基氨基)-喹啉-3-羧酸 | 1025909-31-2

• 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
• 中文名称: 8-氯-4-(3-{4-[2-(2,2,2-三氟-乙氧基)-苯基]-哌嗪-1-基}-丙基氨基)-喹啉-3-羧酸
• 英文名称: 8-Chloro-4-(3-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propylamino)-quinoline-3-carboxylic acid
• 英文别名: 8-Chloro-4-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propylamino]quinoline-3-carboxylic acid
• CAS: 1025909-31-2
• 化学式: C₂₅H₂₆ClF₃N₄O₃
• 分子量: 522.955
• InChiKey: OKIGTOQZVOKEBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  8-氯-4-(3-{4-[2-(2,2,2-三氟-乙氧基)-苯基]-哌嗪-1-基}-丙基氨基)-喹啉-3-羧酸 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 64.4h， 生成 8-Chloro-4-(3-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propylamino)-quinoline-3-carboxylic acid dimethylamide
  参考文献：
  名称：

  N-Arylpiperazinyl-N‘-propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists

  摘要：

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.

  DOI：

  10.1021/jm970166j
• 作为产物：
  描述：

  硝苯酚 在 palladium on activated charcoal 甲醇 、 氢氧化钾 、 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 40.0~140.0 ℃ 、101.33 kPa 条件下， 反应 68.5h， 生成 8-氯-4-(3-{4-[2-(2,2,2-三氟-乙氧基)-苯基]-哌嗪-1-基}-丙基氨基)-喹啉-3-羧酸
  参考文献：
  名称：

  N-Arylpiperazinyl-N‘-propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists

  摘要：

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.

  DOI：

  10.1021/jm970166j