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2-(3-fluoro-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)isoindoline-1,3-dione | 1301178-76-6

中文名称
——
中文别名
——
英文名称
2-(3-fluoro-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)isoindoline-1,3-dione
英文别名
2-[3-fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]isoindoline-1,3-dione;2-[3-Fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]isoindole-1,3-dione
2-(3-fluoro-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)isoindoline-1,3-dione化学式
CAS
1301178-76-6
化学式
C23H26FN3O3
mdl
——
分子量
411.476
InChiKey
TZMFQBUNPNHQRB-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.3
  • 重原子数:
    30
  • 可旋转键数:
    7
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.39
  • 拓扑面积:
    53.1
  • 氢给体数:
    0
  • 氢受体数:
    6

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    N-(3-Fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl)arylcarboxamides as Selective Dopamine D3 Receptor Ligands: Critical Role of the Carboxamide Linker for D3 Receptor Selectivity
    摘要:
    N-(3-Fluoro-4-(4-(2,3-dichloro- or 2-methoxyphenyl)piperazine-1-yl)butyl)arylcarboxamides were prepared and evaluated for binding and function at dopamine D3 receptors (D3Rs) and dopamine D2 receptors (D2Rs). In this series, we discovered some of the most D3R selective compounds reported to date (e.g., 8d and 8j, > 1000-fold D3R-selective over D2R). In addition, chimeric receptor studies further identified the second extracellular (E2) loop as an important contributor to D3R binding selectivity. Further, compounds lacking the carbonyl group in the amide linker were synthesized, and while these amine-linked analogues bound with similar affinities to the amides at D2R, this modification dramatically reduced binding affinities at D3R by > 100-fold (e.g., D3R K-i for 15b = 393 vs for 8j = 2.6 nM), resulting in compounds with significantly reduced D3R selectivity. This study supports a pivotal role for the D3R E2 loop and the carbonyl group in the 4-phenylpiperazine class of compounds and further reveals a point of separation between structure-activity relationships at D3R and D2R.
    DOI:
    10.1021/jm200288r
  • 作为产物:
    参考文献:
    名称:
    [EN] PHENYL CARBAMATES AND THEIR USE AS INHIBITORS OF THE FATTY ACID AMIDE HYDROLASE (FAAH) ENZYME AND MODULATORS OF THE D3 DOPAMINE RECEPTOR (D3DR)
    [FR] PHENYL CARBAMATES ET LEUR UTILISATION COMME INHIBITEURS DE L'ENZYME HYDROLASE D'AMIDES D'ACIDES GRAS (FAAH) ET MODULATEURS DU RÉCEPTEUR D3 DE LA DOPAMINE (D3DR)
    摘要:
    该发明提供了式(I)的化合物或其药用可接受的盐,其中Ar',R1,R2,R3,R4,X,Y如发明描述中所定义,作为多靶点定向配体(MTDLs),同时是脂肪酸酰胺水解酶(FAAH)酶的抑制剂和D3多巴胺受体(D3DR)的调节剂,以及它们的制备方法、配方和治疗应用。
    公开号:
    WO2015007615A1
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文献信息

  • [EN] PHENYL CARBAMATES AND THEIR USE AS INHIBITORS OF THE FATTY ACID AMIDE HYDROLASE (FAAH) ENZYME AND MODULATORS OF THE D3 DOPAMINE RECEPTOR (D3DR)<br/>[FR] PHENYL CARBAMATES ET LEUR UTILISATION COMME INHIBITEURS DE L'ENZYME HYDROLASE D'AMIDES D'ACIDES GRAS (FAAH) ET MODULATEURS DU RÉCEPTEUR D3 DE LA DOPAMINE (D3DR)
    申请人:FOND ISTITUTO ITALIANO DI TECNOLOGIA
    公开号:WO2015007615A1
    公开(公告)日:2015-01-22
    The invention provides compounds of Formula (I) or pharmaceutically acceptable salts thereof wherein Ar', R1, R2, R3, R4, X, Y are as defined in the description of invention, as multi-target directed ligands (MTDLs) that are at the same time inhibitors of the fatty acid amide hydrolase (FAAH) enzyme and modulators of the D3 dopamine receptor (D3DR), their methods of preparation, formulations and therapeutic applications thereof.
    该发明提供了式(I)的化合物或其药用可接受的盐,其中Ar',R1,R2,R3,R4,X,Y如发明描述中所定义,作为多靶点定向配体(MTDLs),同时是脂肪酸酰胺水解酶(FAAH)酶的抑制剂和D3多巴胺受体(D3DR)的调节剂,以及它们的制备方法、配方和治疗应用。
  • PHENYL CARBAMATES AND THEIR USE AS INHIBITORS OF THE FATTY ACID AMIDE HYDROLASE (FAAH) ENZYME AND MODULATORS OF THE D3 DOPAMINE RECEPTOR (D3DR)
    申请人:FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA
    公开号:US20160194296A1
    公开(公告)日:2016-07-07
    The invention provides compounds of Formula (I) or pharmaceutically acceptable salts thereof wherein Ar′, R 1 , R 2 , R 3 , R 4 , X, Y are as defined in the description of invention, as multi-target directed ligands (MTDLs) that are at the same time inhibitors of the fatty acid amide hydrolase (FAAH) enzyme and modulators of the D3 dopamine receptor (D3DR), their methods of preparation, formulations and therapeutic applications thereof.
    本发明提供了化合物I或其药学上可接受的盐,其中Ar′、R1、R2、R3、R4、X、Y的定义如本发明描述中所述,作为多靶点定向配体(MTDLs),同时作为脂肪酸酰胺水解酶(FAAH)酶的抑制剂和D3多巴胺受体(D3DR)的调节剂,以及它们的制备方法、配方和治疗应用。
  • US9828352B2
    申请人:——
    公开号:US9828352B2
    公开(公告)日:2017-11-28
  • <i>N</i>-(3-Fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl)arylcarboxamides as Selective Dopamine D3 Receptor Ligands: Critical Role of the Carboxamide Linker for D3 Receptor Selectivity
    作者:Ashwini K. Banala、Benjamin A. Levy、Sameer S. Khatri、Cheryse A. Furman、Rebecca A. Roof、Yogesh Mishra、Suzy A. Griffin、David R. Sibley、Robert R. Luedtke、Amy Hauck Newman
    DOI:10.1021/jm200288r
    日期:2011.5.26
    N-(3-Fluoro-4-(4-(2,3-dichloro- or 2-methoxyphenyl)piperazine-1-yl)butyl)arylcarboxamides were prepared and evaluated for binding and function at dopamine D3 receptors (D3Rs) and dopamine D2 receptors (D2Rs). In this series, we discovered some of the most D3R selective compounds reported to date (e.g., 8d and 8j, > 1000-fold D3R-selective over D2R). In addition, chimeric receptor studies further identified the second extracellular (E2) loop as an important contributor to D3R binding selectivity. Further, compounds lacking the carbonyl group in the amide linker were synthesized, and while these amine-linked analogues bound with similar affinities to the amides at D2R, this modification dramatically reduced binding affinities at D3R by > 100-fold (e.g., D3R K-i for 15b = 393 vs for 8j = 2.6 nM), resulting in compounds with significantly reduced D3R selectivity. This study supports a pivotal role for the D3R E2 loop and the carbonyl group in the 4-phenylpiperazine class of compounds and further reveals a point of separation between structure-activity relationships at D3R and D2R.
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