1-(4-Ethoxy-phenyl)-piperazine; hydrochloride | 897671-01-1

• 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: 1-(4-Ethoxy-phenyl)-piperazine; hydrochloride
• 英文别名: 1-(4-Ethoxyphenyl)piperazine hydrochloride；1-(4-ethoxyphenyl)piperazine;hydrochloride
• CAS: 897671-01-1
• 化学式: C₁₂H₁₈N₂O*ClH
• 分子量: 242.749
• InChiKey: ZLSUVWJQZDSRLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 1-(4-Ethoxy-phenyl)-piperazine; hydrochloride 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 3-{4-[4-(4-Ethoxy-phenyl)-piperazin-1-yl]-butyl}-5-methoxy-1H-indole
  参考文献：
  名称：

  Indolebutylamines as Selective 5-HT_1A Agonists

  摘要：

  A series of new 1-[4-(indol-3-yl)butyl]-4-arylpiperazines was prepared to identify highly selective and potent 5-HT1A agonists as potential pharmacological tools in studies of mood disorders. The combination of structural elements (indole-alkyl-amine and aryl-piperazine) known to introduce 5-HT1A receptor affinity and the proper selection of substituents (R on the indole moiety and R' on the aryl moiety) led to compounds with high receptor specificity and affinity. In particular, the introduction of the methyl ether or the unsubstituted carboxamide as substituents in position 5 of the indole (R) guaranteed serotonergic 5-HT1A affinity compared to the unsubstituted analogue. Para-substituted arylpiperazines (R') decreased dopaminergic D-2 binding and increased selectivity for the 5-HT1A receptor. Agonistic 5-HT1A receptor activity was confirmed in vivo in the ultrasonic vocalization test, and the results suggest that the introduction of the carboxamide residue leads to better bioavailability than the corresponding methyl ether. 3-{4-[4-(4-Carbamoylphenyl)piperazin-1-yl}butyl}-1H-indole-5-carboxamide 54 was identified as a highly selective 5-HT1A receptor agonist [GTPgammaS, ED50 = 4.7 nM] with nanomolar 5-HT1A affinity [IC50 = 0.9 nM] and selectivity [D-2, IC50 > 850 nM]. 3-{4-[4-(4-Methoxyphenyl)piperazin-1-yl]butyl}-1H-indole-5-carboxamide 45 is one of the most potent and selective 5-HT1A agonists known [5-HT1A, IC50 = 0.09 nM; D-2, IC50 = 140 nM].

  DOI：

  10.1021/jm040792y
• 作为产物：
  描述：

  1-(tert-butyloxycarbonyl)-4-(4-ethoxyphenyl)piperazine 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 1-(4-Ethoxy-phenyl)-piperazine; hydrochloride
  参考文献：
  名称：

  Heterocyclic compounds for the treatment of CNS and cardiovascular

  摘要：

  新型芳香族双环胺化合物的化学式（I）##STR1## 在治疗中枢神经系统疾病、心律失常和心房颤动方面具有用处。

  公开号：

  US05877317A1

文献信息

• Pyrazolone Compounds As Metabotropic Glutamate Receptor Agonists For The Treatment Of Neurological And Psychiatric Disorders
  申请人：Balestra Michael

  公开号：US20090069340A1

  公开（公告）日：2009-03-12

  Compounds of Formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X, and n are as defined for Formula (I) in the description, processes for the preparation of the compounds and new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and the use of the compounds in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction.

  公式（I）的化合物，其中R1，R2，R3，R4，R5，R6，X和n的定义如描述中的公式（I），制备该化合物的过程以及用于制备的新中间体，含有该化合物的制药组合物以及在治疗或预防与谷氨酸功能障碍有关的神经系统和精神障碍中使用该化合物。
• PYRAZOLONE COMPOUNDS AS METABOTROPIC GLUTAMATE RECEPTOR AGONISTS FOR THE TREATMENT OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS
  申请人：AstraZeneca AB

  公开号：EP1833800A1

  公开（公告）日：2007-09-19
• [EN] PYRAZOLONE COMPOUNDS AS METABOTROPIC GLUTAMATE RECEPTOR AGONISTS FOR THE TREATMENT OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS<br/>[FR] COMPOSES DE PYRAZOLONE UTILISES COMME AGONISTES DU RECEPTEUR DE GLUTAMATE METABOTROPIQUE POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES ET PSYCHIATRIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2006071730A1

  公开（公告）日：2006-07-06

  [EN] Compounds of Formula (I), wherein R¹, R², R³, R⁴, R⁵, R⁶, X, and n are as defined for Formula (I) in the description, processes for the preparation of the compounds and new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and the use of the compounds in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction.
  [FR] La présente invention concerne des composés ayant la formule (I), dans laquelle R¹, R², R³, R⁴, R⁵, R⁶, X et n sont tels que définis pour la formule (I) dans la description, des procédés de préparation desdits composés et de nouveaux produits intermédiaires utilisés pour ladite préparation, des compositions pharmaceutiques contenant lesdits composés et l'utilisation desdits composés pour le traitement ou la prévention de troubles neurologiques et psychiatriques associés au dysfonctionnement glutamatergique.
• Indolebutylamines as Selective 5-HT_1A Agonists
  作者：Timo Heinrich、Henning Böttcher、Gerd D. Bartoszyk、Hartmut E. Greiner、Christoph A. Seyfried、Christoph van Amsterdam

  DOI：10.1021/jm040792y

  日期：2004.9.1

  A series of new 1-[4-(indol-3-yl)butyl]-4-arylpiperazines was prepared to identify highly selective and potent 5-HT1A agonists as potential pharmacological tools in studies of mood disorders. The combination of structural elements (indole-alkyl-amine and aryl-piperazine) known to introduce 5-HT1A receptor affinity and the proper selection of substituents (R on the indole moiety and R' on the aryl moiety) led to compounds with high receptor specificity and affinity. In particular, the introduction of the methyl ether or the unsubstituted carboxamide as substituents in position 5 of the indole (R) guaranteed serotonergic 5-HT1A affinity compared to the unsubstituted analogue. Para-substituted arylpiperazines (R') decreased dopaminergic D-2 binding and increased selectivity for the 5-HT1A receptor. Agonistic 5-HT1A receptor activity was confirmed in vivo in the ultrasonic vocalization test, and the results suggest that the introduction of the carboxamide residue leads to better bioavailability than the corresponding methyl ether. 3-4-[4-(4-Carbamoylphenyl)piperazin-1-yl}butyl}-1H-indole-5-carboxamide 54 was identified as a highly selective 5-HT1A receptor agonist [GTPgammaS, ED50 = 4.7 nM] with nanomolar 5-HT1A affinity [IC50 = 0.9 nM] and selectivity [D-2, IC50 > 850 nM]. 3-4-[4-(4-Methoxyphenyl)piperazin-1-yl]butyl}-1H-indole-5-carboxamide 45 is one of the most potent and selective 5-HT1A agonists known [5-HT1A, IC50 = 0.09 nM; D-2, IC50 = 140 nM].
• Heterocyclic compounds for the treatment of CNS and cardiovascular
  申请人：Pharmacia & Upjohn Company

  公开号：US05877317A1

  公开（公告）日：1999-03-02

  Novel aromatic bicyclic amines of formula (I) ##STR1## are useful in treating central nervous system disorders and cardiac arrhythmias and cardiac fibrillation.

  新型芳香族双环胺化合物的化学式（I）##STR1## 在治疗中枢神经系统疾病、心律失常和心房颤动方面具有用处。