5-Bromo-benzofuran-2-carboxylic acid {4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-amide | 644988-82-9

• 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: 5-Bromo-benzofuran-2-carboxylic acid {4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-amide
• 英文别名: 5-bromo-N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-1-benzofuran-2-carboxamide
• CAS: 644988-82-9
• 化学式: C₂₄H₂₈BrN₃O₃
• 分子量: 486.409
• InChiKey: ABNWTYHEAATIEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Bromo-benzofuran-2-carboxylic acid {4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-amide 在 四(三苯基膦)钯 、 六正丁基二锡 、 盐酸 、 <131I>iodide 、 双氧水 作用下， 以 甲苯 、 乙醇 为溶剂， 反应 16.03h， 生成
  参考文献：
  名称：

  Synthesis and radioiodination of selective ligands for the dopamine D3 receptor subtype

  摘要：

  Starting from FAUC 365, a series of iodine substituted heteroaryl carboxamides has been synthesized revealing high affinity and selectivity for the dopamine D3 receptor. Binding data showed a 15-560-fold selectivity for the dopamine D3 over D2. A 2,3-dichloro substitution pattern on the phenylpiperazine moiety led to the highest subtype selectivity, whereas the 2-methoxy substituted compounds showed superior D3 affinity. Suitable precursors were radioiodinated with high radiochemical yields (53-85%) leading to potential imaging agents for the D3 receptor by SPET. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.052
• 作为产物：
  描述：

  4-(4-(2-甲氧基苯基)哌嗪-1-基)丁腈 在 lithium aluminium tetrahydride 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 5-Bromo-benzofuran-2-carboxylic acid {4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-butyl}-amide
  参考文献：
  名称：

  Synthesis and radioiodination of selective ligands for the dopamine D3 receptor subtype

  摘要：

  Starting from FAUC 365, a series of iodine substituted heteroaryl carboxamides has been synthesized revealing high affinity and selectivity for the dopamine D3 receptor. Binding data showed a 15-560-fold selectivity for the dopamine D3 over D2. A 2,3-dichloro substitution pattern on the phenylpiperazine moiety led to the highest subtype selectivity, whereas the 2-methoxy substituted compounds showed superior D3 affinity. Suitable precursors were radioiodinated with high radiochemical yields (53-85%) leading to potential imaging agents for the D3 receptor by SPET. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.052

文献信息

• Synthesis and radioiodination of selective ligands for the dopamine D3 receptor subtype
  作者：Carsten Hocke、Olaf Prante、Stefan Löber、Harald Hübner、Peter Gmeiner、Torsten Kuwert

  DOI：10.1016/j.bmcl.2004.05.052

  日期：2004.8

  Starting from FAUC 365, a series of iodine substituted heteroaryl carboxamides has been synthesized revealing high affinity and selectivity for the dopamine D3 receptor. Binding data showed a 15-560-fold selectivity for the dopamine D3 over D2. A 2,3-dichloro substitution pattern on the phenylpiperazine moiety led to the highest subtype selectivity, whereas the 2-methoxy substituted compounds showed superior D3 affinity. Suitable precursors were radioiodinated with high radiochemical yields (53-85%) leading to potential imaging agents for the D3 receptor by SPET. (C) 2004 Elsevier Ltd. All rights reserved.