4-[4-(2,3-dichlorophenyl)piperazin-1-yl]but-2-yn-1-amine | 595584-31-9

• 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: 4-[4-(2,3-dichlorophenyl)piperazin-1-yl]but-2-yn-1-amine
• CAS: 595584-31-9
• 化学式: C₁₄H₁₇Cl₂N₃
• 分子量: 298.215
• InChiKey: JLFTXXKGVMLNQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.5
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9H-芴-2-羧基 酸 、 4-[4-(2,3-dichlorophenyl)piperazin-1-yl]but-2-yn-1-amine 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 N-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]but-2-ynyl]-9H-fluorene-2-carboxamide
  参考文献：
  名称：

  N-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl, butenyl and butynyl}arylcarboxamides as novel dopamine D3 receptor antagonists

  摘要：

  The dopamine D-3 receptor subtype has been targeted as a potential neurochemical modulator of the behavioral actions of psychomotor stimulants, such as cocaine. Previous synthetic studies provided structural requirements for high affinity binding to D-3 receptors which included a 2,3-dichloro-phenylpiperazine linked to an arylamido function via a butyl chain. To reduce lipo-philicity of these agents and further investigate optimal conformation, a second series of 15 novel ligands was designed that included heteroaromatic substitution and unsaturated alkyl linkers. These compounds were synthesized and evaluated for binding at rat D-3 and D-2 receptors stably expressed in Sf9 cells. D-3 binding affinities ranged from K-i = 0.6-1080 nM, with a broad range of D-3/D-2 selectivities (2-97). The discovery of potent, selective and bioavailable D-3 receptor ligands will provide essential molecular probes to elucidate the role D-3 receptors play in the psychomotor stimulant and reinforcing effects of cocaine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00389-5
• 作为产物：
  描述：

  在 肼 作用下， 以 乙醇 为溶剂， 生成 4-[4-(2,3-dichlorophenyl)piperazin-1-yl]but-2-yn-1-amine
  参考文献：
  名称：

  N-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl, butenyl and butynyl}arylcarboxamides as novel dopamine D3 receptor antagonists

  摘要：

  The dopamine D-3 receptor subtype has been targeted as a potential neurochemical modulator of the behavioral actions of psychomotor stimulants, such as cocaine. Previous synthetic studies provided structural requirements for high affinity binding to D-3 receptors which included a 2,3-dichloro-phenylpiperazine linked to an arylamido function via a butyl chain. To reduce lipo-philicity of these agents and further investigate optimal conformation, a second series of 15 novel ligands was designed that included heteroaromatic substitution and unsaturated alkyl linkers. These compounds were synthesized and evaluated for binding at rat D-3 and D-2 receptors stably expressed in Sf9 cells. D-3 binding affinities ranged from K-i = 0.6-1080 nM, with a broad range of D-3/D-2 selectivities (2-97). The discovery of potent, selective and bioavailable D-3 receptor ligands will provide essential molecular probes to elucidate the role D-3 receptors play in the psychomotor stimulant and reinforcing effects of cocaine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00389-5