1-(4-氯苯乙基)哌啶-4-胺 | 106461-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氯苯乙基)哌啶-4-胺
• 英文名称: 1-(4-chlorophenethyl)piperidin-4-amine
• 英文别名: 1-[2-(4-Chlorophenyl)ethyl]piperidin-4-amine
• CAS: 106461-34-1
• 化学式: C₁₃H₁₉ClN₂
• 分子量: 238.76
• InChiKey: YAXXRTUKMXWTFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯乙基)哌啶-4-胺 在 palladium on activated charcoal 氨 、 氢气 、 sulfur 、 mercury(II) oxide 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (1H-Benzoimidazol-2-yl)-{1-[2-(4-chloro-phenyl)-ethyl]-piperidin-4-yl}-amine
  参考文献：
  名称：

  新的抗组胺N-杂环4-哌啶胺。2. 1-[（（4-氟苯基）甲基] -N-（4-哌啶基）-1H-苯并咪唑-2-a的合成及抗组胺活性。

  摘要：

  描述了一系列的1-[（4-氟苯基）甲基] -N-（4-哌啶基）-1H-苯并咪唑-2-酰胺的合成及其在体内的抗组胺活性的初步评估。通过不同的合成方法从1、4、10或55开始获得标题化合物。苯并咪唑环（84-87）的苯基核上的取代是通过两种不同的方法实现的。口服和/或皮下给药后，通过化合物48/80在大鼠中的致死性试验和豚鼠中抗组胺的致死性试验评估体内抗组胺活性。在豚鼠中研究了三种化合物（4、51和55）的作用持续时间。化合物51“阿司咪唑”，在组胺和5-羟色胺诱导的皮肤反应以及大鼠的散瞳活性方面也进行了研究，并在各种系统中测试了与组胺拮抗作用无关的周围和中枢作用。已选择阿司咪唑用于临床研究。

  DOI：

  10.1021/jm00150a029
• 作为产物：
  描述：

  2-(4-氯苯基)氯乙烷 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(4-氯苯乙基)哌啶-4-胺
  参考文献：
  名称：

  Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species

  摘要：

  The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl(1)-NH-Aryl(2) scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.006

文献信息

• [EN] USE OF SUBSTANCE P ANTAGONISTS FOR TREATING SOCIAL PHOBIA<br/>[FR] UTILISATION D'ANTAGONISTES DE LA SUBSTANCE P POUR TRAITER LA PHOBIE SOCIALE
  申请人：NOVARTIS AG

  公开号：WO1997045119A1

  公开（公告）日：1997-12-04

  (EN) The invention relates to the use of a compound of formula (I) or of a pharmaceutically utilizable salt thereof, in which R1 is an unsubstituted or substituted aralkyl, aryloxyalkyl, heteroaralkyl, aroyl, heteroaroyl, cycloalkylcarbonyl, aralkanoyl, heteroarylalkanoyl, aralkoxycarbonyl or arylcarbamoyl radical or the acyl radical of an $g(a)-amino acid which is unsubstituted or N-substituted by lower alkanoyl or carbamoyl-lower-alkanoyl; R2 is cycloalkyl or an unsubstituted or substituted aryl or heteroaryl radical; R3 is hydrogen, alkyl, carbamoyl or an alkanoyl or alkenoyl radical which is unsubstituted or substituted by carboxyl or esterified or amidated carboxyl; R4 is an unsubstituted or substituted aryl or unhydrogenated or partially hydrogenated heteroaryl radical; X1 is methylene, ethylene, a direct linkage, a carbonyl group which may be ketalized, or an unetherified or etherified hydroxymethylene group; X2 is alkylene, carbonyl or a direct linkage; and X3 is carbonyl, oxo-lower-alkylene, oxo(aza)-lower-alkylene or an alkylene radical which is unsubstituted or substituted by phenyl, hydroxymethyl, carboxyl which may be esterified or amidated, or by hydroxyl in a position higher than $g(a); for producing pharmaceutical products for the treatment of social phobia.(FR) L'invention concerne l'utilisation d'un composé selon la formule (I) ou d'un sel pharmaceutiquement acceptable de ce dernier. Dans la formule, R1 est un radical aralkyle, aryloxyalkyle, hétéroaralkyle, aroyle, hétéroaroyle, cycloalkylcarbonyle, aralcanoyle, hétéroarylalcanoyle, aralcoxycarbonyle ou arylcarbamoyle non substitué ou substitué, ou le radical acyle d'un acide $g(a)-aminé qui n'est pas substitué ou qui est N-substitué par un alcanoyle inférieur ou un carbamoyl-acanoyle inférieur; R2 représente cycloalkyle ou un radical aryle ou hétéroaryle non substitué ou substitué; R3 représente hydrogène, alkyle, carbamoyle ou un radical alcanoyle ou alcénoyle qui n'est pas substitué ou substitué par carboxyle ou carboxyle estérifié ou amidé; R4 est un aryle non substitué ou substitué ou un radical hétéroaryle non hydrogéné ou partiellement hydrogéné; X1 est méthylène, éthylène, une liaison directe, un groupe carbonyle qui peut être cétalisé ou un groupe hydroxyméthylène éthérifié ou non éthérifié; X2 représente alkylène, carbonyle ou une liaison directe; et X3 est carbonyle, oxo-alkylène inférieur, oxo(aza)-alkylène inférieur ou un radical alkylène qui n'est pas substitué ou est substitué par du phényle, hydroxyméthyle, carboxyle qui peut être estérifié, ou amidé, ou par de l'hydroxyle dans une position supérieure à $g(a). Ce composé est utilisé pour fabriquer des produits pharmaceutiques pour traiter la phobie sociale.
• Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species
  作者：Thuy Nguyen、Tianming Yang、Mei-Lin Go

  DOI：10.1016/j.bmcl.2014.02.006

  日期：2014.4

  The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl(1)-NH-Aryl(2) scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds. (C) 2014 Elsevier Ltd. All rights reserved.
• New antihistaminic N-heterocyclic 4-piperidinamines. 2. Synthesis and antihistaminic activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amines
  作者：Frans Janssens、Joseph Torremans、Marcel Janssen、Raymond A. Stokbroekx、Marcel Luyckx、Paul A. J. Janssen

  DOI：10.1021/jm00150a029

  日期：1985.12

  The synthesis of a series of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-ami nes and the preliminary evaluation of their in vivo antihistamine activity are described. The title compounds were obtained starting from either 1, 4, 10, or 55 by different synthetic methods. Substitution on the phenyl nucleus of the benzimidazole ring (84-87) was achieved by two different approaches. The

  描述了一系列的1-[（4-氟苯基）甲基] -N-（4-哌啶基）-1H-苯并咪唑-2-酰胺的合成及其在体内的抗组胺活性的初步评估。通过不同的合成方法从1、4、10或55开始获得标题化合物。苯并咪唑环（84-87）的苯基核上的取代是通过两种不同的方法实现的。口服和/或皮下给药后，通过化合物48/80在大鼠中的致死性试验和豚鼠中抗组胺的致死性试验评估体内抗组胺活性。在豚鼠中研究了三种化合物（4、51和55）的作用持续时间。化合物51“阿司咪唑”，在组胺和5-羟色胺诱导的皮肤反应以及大鼠的散瞳活性方面也进行了研究，并在各种系统中测试了与组胺拮抗作用无关的周围和中枢作用。已选择阿司咪唑用于临床研究。