1-(2-fluoro-4-(2-methoxyethoxy)phenyl)piperazine | 515160-73-3

• 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-(2-fluoro-4-(2-methoxyethoxy)phenyl)piperazine
• 英文别名: Piperazine, 1-[2-fluoro-4-(2-methoxyethoxy)phenyl]-；1-[2-fluoro-4-(2-methoxyethoxy)phenyl]piperazine
• CAS: 515160-73-3
• 化学式: C₁₃H₁₉FN₂O₂
• 分子量: 254.304
• InChiKey: LUDFOQRNTPFENE-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±42.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-fluoro-4-(2-methoxyethoxy)phenyl)piperazine 、 5-amino-7-(2-chloroethyl)-2-[(3-chlorophenyl)methyl]-2,7-dihydro-3H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-3-one 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-Amino-4-[(3-chlorophenyl)methyl]-10-[2-[4-[2-fluoro-4-(2-methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-3,4,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,7,11-tetraen-5-one
  参考文献：
  名称：

  Potent and selective adenosine A2A receptor antagonists: [1,2,4]-triazolo[4,3-c]pyrimidin-3-ones

  摘要：

  Antagonism of the adenosine A(2A) receptor affords a possible treatment of Parkinson's disease. In the course of investigating pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A(2A) antagonists, we prepared [1,2,4]-triazolo[4,3-c]pyrimidin-3-ones with potent and selective (vs A(1)) A(2A) antagonist activity. Structure-activity relationships are described for this series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.045
• 作为产物：
  描述：

  4-溴-3-氟苯酚 在 palladium diacetate 、 Pd(tBu)3 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 1-(2-fluoro-4-(2-methoxyethoxy)phenyl)piperazine
  参考文献：
  名称：

  2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1

  摘要：

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.086

文献信息

• 2-Heteroaryl-pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2a receptor antagonists
  申请人：Neustadt R. Bernard

  公开号：US20070066620A1

  公开（公告）日：2007-03-22

  Compounds having the structural formula I or a pharmaceutically acceptable salt thereof, wherein R is R 1 -isoxazolyl, R 1 -oxadiazolyl, R 1 -dihydrofuranyl, R 1 -pyrazolyl, R 1 -imidazolyl, R 1 -pyrazinyl or R 1 -pyrimidinyl; R 1 is 1, 2 or 3 substituents selected from H, alkyl, alkoxy and halo; Z is optionally substituted-aryl, or optionally substituted-heteroaryl; are disclosed, as well as their use in the treatment of central nervous system diseases, in particular Parkinson's disease and Extra Pyramidal Syndrome, pharmaceutical compositions comprising them, and combinations with other agents.

  具有结构式I或其药用可接受盐的化合物，其中R是R1-异噁唑基、R1-噁唑啉基、R1-二氢呋喃基、R1-吡唑基、R1-咪唑基、R1-吡啶基或R1-嘧啶基；R1是从H、烷基、烷氧基和卤代中选择的1、2或3个取代基；Z是可选择取代的芳基或可选择取代的杂芳基；公开了这些化合物及其在治疗中枢神经系统疾病，特别是帕金森病和额外锥体综合征中的用途，包括它们的药物组合物和与其他药剂的组合。
• [EN] PYRAZOLOTRIAZOLOPYRIMIDINE DERIVATIVES AS A2A RECEPTOR ANTAGONIST<br/>[FR] DÉRIVÉS DE PYRAZOLOTRIAZOLOPYRIMIDINE EN TANT QU'ANTAGONISTE DU RÉCEPTEUR A2A
  申请人：BEIGENE LTD

  公开号：WO2020020097A1

  公开（公告）日：2020-01-30

  Disclosed herein is a pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as A2A receptor antagonist, and a pharmaceutical composition comprising the same. Also disclosed herein is a method of treating cancer using the pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as A2A receptor antagonist.

  本文揭示了一种吡唑三唑吡嘧啶衍生物或其立体异构体，或其药学上可接受的盐，可用作A2A受体拮抗剂，以及包含该物质的药物组合物。本文还揭示了一种使用该吡唑三唑吡嘧啶衍生物或其立体异构体，或其药学上可接受的盐作为A2A受体拮抗剂治疗癌症的方法。
• HETEROCYCLYL SUBSTITUTED ARYLINDENOPYRIMIDINES AND THEIR USE AS HIGHLY SELECTIVE ADENOSINE A2a RECEPTOR ANTAGONISTS
  申请人：JACKSON Paul F.

  公开号：US20110105493A1

  公开（公告）日：2011-05-05

  This invention relates to a novel arylindenopyrimidine, A, and its therapeutic and prophylactic uses. Disorders treated and/or prevented include Parkinson's Disease. wherein X, R 2 , R 3 , and R 4 are as defined in the specification.

  这项发明涉及一种新的芳基吲哚吡啶，A，以及其治疗和预防用途。治疗和/或预防的疾病包括帕金森病。其中X，R2，R3和R4如规范中定义。
• 2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1
  作者：Julius J. Matasi、John P. Caldwell、Hongtao Zhang、Ahmad Fawzi、Mary E. Cohen-Williams、Geoffrey B. Varty、Deen B. Tulshian

  DOI：10.1016/j.bmcl.2005.05.086

  日期：2005.8

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.
• Potent, selective, and orally active adenosine A2A receptor antagonists: Arylpiperazine derivatives of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines
  作者：Bernard R. Neustadt、Jinsong Hao、Neil Lindo、William J. Greenlee、Andrew W. Stamford、Deen Tulshian、Ennio Ongini、John Hunter、Angela Monopoli、Rosalia Bertorelli、Carolyn Foster、Leyla Arik、Jean Lachowicz、Kwokei Ng、Kung-I Feng

  DOI：10.1016/j.bmcl.2006.11.083

  日期：2007.3

  Antagonism of the adenosine A2A receptor offers great promise in the treatment of Parkinson's disease. Employing the known pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A2A antagonist SCH 58261 as a starting point, we identified the potent and selective (vs. A1) antagonist 11h, orally active in the rat haloperidol-induced catalepsy model. We further optimized this lead to the methoxyethoxyethyl ether 12a (SCH 420814), which shows broad selectivity, good pharmacokinetic properties, and excellent in vivo activity.