N-[3-[4-(4-fluoro-2-methoxyphenyl)-1-piperazinyl]propyl]-phthalimide | 102392-12-1

• 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: N-[3-[4-(4-fluoro-2-methoxyphenyl)-1-piperazinyl]propyl]-phthalimide
• 英文别名: 2-[3-[4-(4-Fluoro-2-methoxyphenyl)piperazin-1-yl]propyl]isoindole-1,3-dione
• CAS: 102392-12-1
• 化学式: C₂₂H₂₄FN₃O₃
• 分子量: 397.449
• InChiKey: CYAPKGISOUOAGP-UHFFFAOYSA-N

物化性质

• 沸点：
  554.1±50.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[3-[4-(4-fluoro-2-methoxyphenyl)-1-piperazinyl]propyl]-phthalimide 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 xylene 为溶剂， 反应 21.0h， 生成 8-Cyano-4-{3-[4-(4-fluoro-2-methoxy-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：

  1-(4-氟-2-甲氧基苯基)哌嗪 以18.1 g (96%)的产率得到N-[3-[4-(4-fluoro-2-methoxyphenyl)-1-piperazinyl]propyl]-phthalimide
  参考文献：
  名称：

  Isoindolinyl-alkyl-piperazines

  摘要：

  这项发明通常涉及isoindolinyl-烷基哌嗪化合物，一般以以下式子为特征：##STR1## 其中X是卤素或三氟甲基；n是一个从2到5的整数；Y是##STR2## 其中R.sub.1是氢、卤素、较低烷基、较低烷氧基、三氟甲基、氰基；R.sub.2是氢、卤素、较低烷基、较低烷氧基；R.sub.3是氢、氰基。这些化合物可用作利尿剂和/或降压药。

  公开号：

  US04585773A1

文献信息

• US4585773A
  申请人：——

  公开号：US4585773A

  公开（公告）日：1986-04-29
• Isoindolinyl-alkyl-piperazines
  申请人：Bristol-Myers Company

  公开号：US04585773A1

  公开（公告）日：1986-04-29

  The invention is generally concerned with isoindolinyl-alkylpiperazine compounds generally characterized by the formula ##STR1## wherein X is halogen or trifluoromethyl; n is an integer ranging from 2 to 5; Y is ##STR2## in which R.sub.1 is hydrogen, halogen, lower alkyl, lower alkoxy, trifluoromethyl, cyano; R.sub.2 is hydrogen, halogen, lower alkyl, lower alkoxy; and R.sub.3 is hydrogen, cyano. These compounds are useful as diuretic and/or antihypertensive agents.

  这项发明通常涉及isoindolinyl-烷基哌嗪化合物，一般以以下式子为特征：##STR1## 其中X是卤素或三氟甲基；n是一个从2到5的整数；Y是##STR2## 其中R.sub.1是氢、卤素、较低烷基、较低烷氧基、三氟甲基、氰基；R.sub.2是氢、卤素、较低烷基、较低烷氧基；R.sub.3是氢、氰基。这些化合物可用作利尿剂和/或降压药。
• <i>N-</i>Arylpiperazinyl-<i>N</i>‘<i>-</i>propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists
  作者：Todd R. Elworthy、Anthony P. D. W. Ford、Gary W. Bantle、David J. Morgans,、Rachel S. Ozer、Wylie S. Palmer、David B. Repke、Magarita Romero、Leticia Sandoval、Eric B. Sjogren、Francisco X. Talamás、Alfredo Vazquez、Helen Wu、Nicolas F. Arredondo、David R. Blue,、Andrea DeSousa、Lisa M. Gross、M. Shannon Kava、John D. Lesnick、Rachel L. Vimont、Timothy J. Williams、Quan-Ming Zhu、Jürg R. Pfister、David E. Clarke

  DOI：10.1021/jm970166j

  日期：1997.8.1

  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.