1-amino-3-[4-(2-isopropoxyphenyl)piperazin-1-yl]propane | 216252-71-0

• 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-amino-3-[4-(2-isopropoxyphenyl)piperazin-1-yl]propane
• 英文别名: 3-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-propylamine；3-[4-(2-isopropoxyphenyl)piperazin-1-yl]propylamine；3-[4-(2-Propan-2-yloxyphenyl)piperazin-1-yl]propan-1-amine
• CAS: 216252-71-0
• 化学式: C₁₆H₂₇N₃O
• 分子量: 277.41
• InChiKey: FLYQHSIFFNNCHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  414.4±45.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  41.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  柠康酸酐 、 1-amino-3-[4-(2-isopropoxyphenyl)piperazin-1-yl]propane 以 甲苯 为溶剂， 反应 4.0h， 以82%的产率得到1-{3-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-propyl}-3-methyl-pyrrol-2,5-dione
  参考文献：
  名称：

  [EN] 1-ALKYLPIPERAZINYL-PYRROLIDIN-2, 5-DIONE DERIVATIVES AS ADRENERGIC RECEPTOR ANTAGONIST
  [FR] DERIVES DE 1-ALKYLPIPERAZINYL-PYRROLIDIN-2,5-DIONE UTILES COMME ANTAGONISTES DU RECEPTEUR ADRENERGIQUE

  摘要：

  本公开的化合物具有以下结构（I），可以作为α1a和/或α1d肾上腺素受体拮抗剂，并可用于治疗良性前列腺增生及相关症状。本公开的化合物还可用于治疗与或不伴有良性前列腺增生相关的下尿路症状。本发明还涉及一种制备本公开的化合物的方法，以及含有这些化合物的药物组合物。

  公开号：

  WO2005037281A1
• 作为产物：
  描述：

  3-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-propionitrile 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以97%的产率得到1-amino-3-[4-(2-isopropoxyphenyl)piperazin-1-yl]propane
  参考文献：
  名称：

  [EN] 1-ALKYLPIPERAZINYL-PYRROLIDIN-2, 5-DIONE DERIVATIVES AS ADRENERGIC RECEPTOR ANTAGONIST
  [FR] DERIVES DE 1-ALKYLPIPERAZINYL-PYRROLIDIN-2,5-DIONE UTILES COMME ANTAGONISTES DU RECEPTEUR ADRENERGIQUE

  摘要：

  本公开的化合物具有以下结构（I），可以作为α1a和/或α1d肾上腺素受体拮抗剂，并可用于治疗良性前列腺增生及相关症状。本公开的化合物还可用于治疗与或不伴有良性前列腺增生相关的下尿路症状。本发明还涉及一种制备本公开的化合物的方法，以及含有这些化合物的药物组合物。

  公开号：

  WO2005037281A1

文献信息

• [EN] ALPHA, OMEGA-DICARBOXIMIDE DERIVATIVES AS USEFUL URO-SELECTIVE Alpha1Alpha ADRENOCEPTOR BLOCKERS<br/>[FR] DERIVES D'ALPHA, OMEGA-DICARBOXIMIDE UTILES EN TANT QU'INHIBITEURS UROSELECTIFS DE L'ADRENO-RECEPTEUR <1?
  申请人：RANBAXY LAB LTD

  公开号：WO2003084928A1

  公开（公告）日：2003-10-16

  Novel α,ω-dicarboximide derivatives which selectively inhibit binding to the α-1A adrenergic receptor, a receptor which has been shown to be important in the treatment of benign prostatic hyperplasia. The compounds of the present invention are potentially useful in the treatment of benign prostatic hyperplasia.

  新型α, ω-二羧酰亚胺衍生物，可选择性地抑制与α-1A肾上腺素受体的结合，该受体已被证明在良性前列腺增生的治疗中很重要。本发明的化合物有望用于治疗良性前列腺增生。
• Phthalimido arylpiperazines useful in the treatment of benign prostatic hyperplasia
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06362338B1

  公开（公告）日：2002-03-26

  This invention relates to a series of substituted piperazines of Formula II, as well as enantiomers thereof These compounds are useful in the manufacture of pharmaceutical compositions.

  这项发明涉及到一系列Formula II的替代哌嗪，以及其对映体。这些化合物在制药组合物的制造中是有用的。
• 3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy -pyridine, pyrimidine and benzene derivatives as alpha1-adrenoceptor antagonists
  申请人：F. Hoffmann-La Roche AG

  公开号：EP0711757A1

  公开（公告）日：1996-05-15

  The present invention relates to novel α₁-adrenoceptor antagonists of Formula I: in which: p is 0 or 1; t is 0, 1 or 2; X is O, S or NR⁶ (in which R⁶ is hydro or (C₁₋₆)alkyl); Y and Z are independently CH or N; R¹ is hydro, hydroxy, halo, nitro, amino, cyano, (C₁₋₄)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, (C₃₋₆)cycloalkyl(C₁₋₄)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl(C₁₋₄)alkyl, heteroaryl(C₁₋₄)alkyl, (C₁₋₆)alkyloxy, (C₃₋₆)cycloalkyloxy, (C₃₋₆)cycloalkyl(C₁₋₄)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl(C₁₋₄)alkyloxy or heteroaryl(C₁₋₄)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano); R² is hydro, hydroxy, halo, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms); R³ is -C(O)R⁷ (wherein R⁷ is (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, di(C₁₋₄)alkylamino, N-(C₁₋₄)alkyl-N-(C₁₋₄)alkyloxyamino, (C₁₋₄)alkyl((C₁₋₄)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl); R⁴ is halo, hydroxy, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy; and R⁵ is (C₁₋₆)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.

  本发明涉及式 I 的新型 α₁-肾上腺素受体拮抗剂： 其中 p 是 0 或 1； t 是 0、1 或 2 X 是 O、S 或 NR⁶（其中 R⁶ 是氢或 (C₁₋₆)烷基）； Y 和 Z 独立地为 CH 或 N； R¹是氢、羟基、卤代、硝基、氨基、氰基、(C₁₋₄)烷硫基、乙酰氨基、三氟乙酰氨基、甲磺酰氨基、(C₁₋₆)烷基、(C₃₋₆)环烷基、(C₃₋₆)环烷基(C₁₋₄)烷基、噁唑-2-基、芳基、杂芳基、芳基(C₁₋₄)烷基、杂芳基(C₁₋₄)烷基、(C₁₋₆)烷氧基、(C₃₋₆)环烷氧基、(C₃₋₆)环烷基(C₁₋₄)烷氧基，2-丙炔氧基，芳基氧基，杂芳基氧基、芳基（C₁₋₄）烷氧基或杂芳基（C₁₋₄）烷氧基（其中烷基任选被一至三个卤原子取代，芳基或杂芳基任选被一至两个独立选自卤素和氰基的取代基取代）； R² 是氢、羟基、卤代、氰基、(C₁₋₆)烷基或(C₁₋₆)烷氧基（其中烷基任选被一至三个卤原子取代）； R³ 是 -C(O)R⁷（其中 R⁷ 是 (C₁₋₆)烷基、(C₃₋₆)环烷基、二(C₁₋₄)烷基氨基、N-(C₁₋₄)烷基-N-(C₁₋₄)烷氧基氨基、(C₁₋₄)烷基((C₁₋₄烷氧基)氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基)； R⁴ 是卤素、羟基、氰基、(C₁₋₆)烷基或 (C₁₋₆)烷氧基；和 R⁵ 是 (C₁₋₆)烷基；及其药学上可接受的盐和 N-氧化物。
• Alpha, omega-dicarboximide derivatives as useful uro-selective a1a adrenoceptor blockers
  申请人：Salman Mohammad

  公开号：US20050228180A1

  公开（公告）日：2005-10-13

  Novel α,β-dicarboximide derivatives which selectively inhibit binding to the α- ,1A? adrenergic receptor, a receptor which has been shown to be important in the treatment of benign prostatic hyperplasia. The compounds of the present invention are potentially useful in the treatment of benign prostatic hyperplasia.

  新型α,β-二甲酰亚胺衍生物可选择性地抑制与α-,1A? 1A?肾上腺素能受体的结合，该受体已被证明在治疗良性前列腺增生症中具有重要作用。本发明的化合物可用于治疗良性前列腺增生症。
• Design, synthesis and biological evaluation of pyridine-phenylpiperazines: A novel series of potent and selective α1a-adrenergic receptor antagonist
  作者：Gee-Hong Kuo、Catherine Prouty、William V Murray、Virginia Pulito、Linda Jolliffe、Peter Cheung、Sally Varga、Mary Evangelisto、Charles Shaw

  DOI：10.1016/s0968-0896(00)00151-6

  日期：2000.9

  Beginning from the screening hit and literature alpha(1)-adrenergic compounds, a hybridized basic skeleton A was proposed as the pharmacophore for potent and selective alpha(1a)-AR antagonists. Introduction of a hydroxy group to increase the flexibility afforded B which served as the screening model and resulted in the identification of the second-generation lead 1. Using the Topliss approach, a number of potent and selective alpha(1a)-AR antagonists were discovered. In all cases, binding affinity and selectivity at the alpha(1a)-AR of S-hydroxy enantiomers were higher than the R-hydroxy enantiomers. As compared to the des-hydroxy analogues, the S-hydroxy enantiomers displayed comparable potency and better selectivity at alpha(1a)-AR. The S-hydroxy enantiomer 17 (K-i = 0.79 nM; alpha(1b)/alpha(1a) = 800; alpha(1d)/alpha(1a) = 104) was slightly less potent but much more selective at alpha(1a)-AR than tamsulosin (K-i = 0.13 nM, alpha(1b)/alpha(1a) = 15, alpha(1d)/alpha(1a) = 1.4). Compound 17 displayed higher selectivity in inhibiting rat prostate contraction over rat aorta contraction and also exhibited a higher degree of uroselectivity than tamsulosin in the anesthetized dog model. (C) 2000 Elsevier Science Ltd. All rights reserved.