1,3-Dimethyl-4-(3-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid dimethylamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1,3-Dimethyl-4-(3-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid dimethylamide
• 英文别名: N,N,1,3-tetramethyl-4-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propylamino]pyrazolo[3,4-b]pyridine-5-carboxamide
• 化学式: C₂₆H₃₄F₃N₇O₂
• 分子量: 533.597
• InChiKey: BSUZYOKJXFBXNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  硝苯酚 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 一水合肼 、 sodium iodide 作用下， 以 乙醇 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 90.0~140.0 ℃ 、101.33 kPa 条件下， 反应 59.5h， 生成 1,3-Dimethyl-4-(3-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperazin-1-yl}-propylamino)-1H-pyrazolo[3,4-b]pyridine-5-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