2-Amino-1-(4-phenethylpiperazin-1-yl)ethanone | 189762-05-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Amino-1-(4-phenethylpiperazin-1-yl)ethanone
• 英文别名: 2-amino-1-[4-(2-phenylethyl)piperazin-1-yl]ethanone
• CAS: 189762-05-8
• 化学式: C₁₄H₂₁N₃O
• 分子量: 247.34
• InChiKey: RFEZNZURLKCXQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Amino-1-(4-phenethylpiperazin-1-yl)ethanone 、 异喹啉-5-磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-oxo-2-(4-phenethylpiperazin-1-yl)ethyl)isoquinoline-5-sulfonamide
  参考文献：
  名称：

  From Tyrosine to Glycine:  Synthesis and Biological Activity of Potent Antagonists of the Purinergic P2X₇ Receptor

  摘要：

  The characterization of the native and recombinant P2X(7) receptor continues to be hindered by the lack of specific and subtype-selective antagonists with a "druglike" profile. However, a tyrosine derivative named KN-62 exhibits selective P2X(7) receptor-blocking properties. As a molecular simplification of KN-62, the present study was designed to evaluate the functional antagonistic properties of a novel series of glycine derivatives characterized by the presence of different phenyl-substituted piperazine moieties. Antagonistic activity of these glycine derivatives was tested on HEK293 cells transfected with the human P2X(7) receptor. The most potent P2X(7) receptor antagonist identified in this study (compound 4g) contains an o-fluorine substituent on the phenylpiperazine moiety and had an IC50 of 12.1 nM. The biological responses investigated were ATP-dependent Ca2+ influx across the plasma membrane and ethidium bromide uptake.

  DOI：

  10.1021/jm070443e
• 作为产物：
  描述：

  benzyl ester of [2-oxo-2-(4-phenethylpiperazin-1-yl)ethyl]carbamic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-Amino-1-(4-phenethylpiperazin-1-yl)ethanone
  参考文献：
  名称：

  From Tyrosine to Glycine:  Synthesis and Biological Activity of Potent Antagonists of the Purinergic P2X₇ Receptor

  摘要：

  The characterization of the native and recombinant P2X(7) receptor continues to be hindered by the lack of specific and subtype-selective antagonists with a "druglike" profile. However, a tyrosine derivative named KN-62 exhibits selective P2X(7) receptor-blocking properties. As a molecular simplification of KN-62, the present study was designed to evaluate the functional antagonistic properties of a novel series of glycine derivatives characterized by the presence of different phenyl-substituted piperazine moieties. Antagonistic activity of these glycine derivatives was tested on HEK293 cells transfected with the human P2X(7) receptor. The most potent P2X(7) receptor antagonist identified in this study (compound 4g) contains an o-fluorine substituent on the phenylpiperazine moiety and had an IC50 of 12.1 nM. The biological responses investigated were ATP-dependent Ca2+ influx across the plasma membrane and ethidium bromide uptake.

  DOI：

  10.1021/jm070443e

文献信息

• [EN] ARYL-PIPERAZINE CYCLIC AMINE DERIVATIVES, PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] DERIVES D'AMINES CYCLIQUES D'ARYL-PIPERAZINES, LEUR PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：PIERRE FABRE MEDICAMENT

  公开号：WO1997014689A1

  公开（公告）日：1997-04-24

  (EN) Derivatives of general formula (I), wherein R1 = H or C1-6 alkyl; R2 is a straight or branched C1-8 alkyl residue, C3-8 cycloalkyl, aryl, arylalkyl, arylcarbonyl or, when X is not nitrogen, arylether; each of R3 and R4, which are the same or different, is hydrogen or a group selected from straight or branched alkyl, alkoxy, trifluoromethyl or halogen; X-Y is CH, CH-CH2, C=CH, NCH2 or NCH2CH2; Z = Z1-(CH2)m-Z2, Z1-Ar-(CH2)n-Z2, Z1-(CH2)m-1-CONH-, Z1-Ar-(CH2)n-1-CONH-, -CH(R5)-NHCO-Z2 wherein Z1 and Z2, which are the same or different, may be absent or are O or NH; m is an integer from 2 to 8; and n is an integer from 1 to 6.(FR) La présente invention concerne des dérivés de formule générale (I) dans laquelle R1 = H, C1-C6 alkyle; R2 représente un résidu alkyle, linéaire ou ramifié comprenant de 1 à 8 atomes de carbone, un cycloalkyle (comprenant de 3 à 8 atomes de carbone), un aryle, un arylalkyle, un arylcarbonyle ou encore un aryle éther lorsque X est différent d'un azote, R3 et R4 identiques ou différents représentent un hydrogène ou un groupe choisi parmi un alkyle linéaire ou ramifié, un alcoxy, trifluorométhyle ou halogène, X-Y représente CH, CH-CH2, C=CH, NCH2 ou NCH2CH2; Z = Z1-(CH2)m-Z2, Z1-Ar-(CH2)n-Z2, Z1-(CH2)m-1-CONH-, Z1-Ar-(CH2)n-1-CONH-, -CH(R5)-NHCO-Z2 dans lesquels Z1 et Z2, identiques ou différents peuvent être omis ou représenter O ou NH, m représente un nombre entier compris entre 2 et 8, n représente un nombre entier compris entre 1 et 6.
• From Tyrosine to Glycine:  Synthesis and Biological Activity of Potent Antagonists of the Purinergic P2X₇ Receptor
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Delia Preti、Olga Cruz-Lopez、Mojgan Aghazadeh Tabrizi、Allan R. Moorman、Stefania Gessi、Eleonora Fogli、Valeria Sacchetto、Pier Andrea Borea

  DOI：10.1021/jm070443e

  日期：2007.7.1

  The characterization of the native and recombinant P2X(7) receptor continues to be hindered by the lack of specific and subtype-selective antagonists with a "druglike" profile. However, a tyrosine derivative named KN-62 exhibits selective P2X(7) receptor-blocking properties. As a molecular simplification of KN-62, the present study was designed to evaluate the functional antagonistic properties of a novel series of glycine derivatives characterized by the presence of different phenyl-substituted piperazine moieties. Antagonistic activity of these glycine derivatives was tested on HEK293 cells transfected with the human P2X(7) receptor. The most potent P2X(7) receptor antagonist identified in this study (compound 4g) contains an o-fluorine substituent on the phenylpiperazine moiety and had an IC50 of 12.1 nM. The biological responses investigated were ATP-dependent Ca2+ influx across the plasma membrane and ethidium bromide uptake.