6-Chloro-N-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butyl}-nicotinamide | 869383-25-5

• 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: 6-Chloro-N-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butyl}-nicotinamide
• CAS: 869383-25-5
• 化学式: C₂₀H₂₃Cl₃N₄O
• 分子量: 441.788
• InChiKey: DDFGRKWIYAYTEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-Chloro-N-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butyl}-nicotinamide 在 fluorine-18 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of 18F-labeled dopamine D3 receptor ligands as potential PET imaging agents

  摘要：

  A series of fluoro substituted aryl carboxamides was synthesized revealing high affinity for the dopamine D3 receptor. In contrast to 2-methoxy substitution, a 2,3-dichloro substitution pattern at the phenylpiperazine moiety induces a 10-fold increase of D3 affinity which is expressed by K-i values of 0.53, 1.1, and 9.0 nM for 8b, 8d, and 8f. Applying aromatic F-18-for-Br(Cl) substitution, high radiochemical yields between 76-82% were obtained for [F-18]8c-f. The most promising ligand, [F-18]8d, was used as imaging agent of the D3 receptor in vitro. However, due to the lack of specific binding, further studies should aim at the development of radioligands with improved D3 receptor selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.037
• 作为产物：
  描述：

  4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyronitrile 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 6-Chloro-N-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butyl}-nicotinamide
  参考文献：
  名称：

  Synthesis and evaluation of 18F-labeled dopamine D3 receptor ligands as potential PET imaging agents

  摘要：

  A series of fluoro substituted aryl carboxamides was synthesized revealing high affinity for the dopamine D3 receptor. In contrast to 2-methoxy substitution, a 2,3-dichloro substitution pattern at the phenylpiperazine moiety induces a 10-fold increase of D3 affinity which is expressed by K-i values of 0.53, 1.1, and 9.0 nM for 8b, 8d, and 8f. Applying aromatic F-18-for-Br(Cl) substitution, high radiochemical yields between 76-82% were obtained for [F-18]8c-f. The most promising ligand, [F-18]8d, was used as imaging agent of the D3 receptor in vitro. However, due to the lack of specific binding, further studies should aim at the development of radioligands with improved D3 receptor selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.037