3-methoxy-N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-4-(pent-4-yn-1-yloxy)benzamide | 1346263-97-5

• 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: 3-methoxy-N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-4-(pent-4-yn-1-yloxy)benzamide
• CAS: 1346263-97-5
• 化学式: C₂₈H₃₇N₃O₄
• 分子量: 479.619
• InChiKey: KVUYNJPMXPZIBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.27
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-methoxy-N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-4-(pent-4-yn-1-yloxy)benzamide 、 4-[3-[1-(8-azidooctyl)-1H-1,2,3-triazol-4-yl]propoxy]-N-[4-[(indan-2-yl)(propyl)amino]butyl]-3-methoxybenzamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 以82%的产率得到4-[3-[1-[8-[4-[3-[4-[[[4-[(indan-2-yl)(propyl)amino]butyl]amino]carbonyl]-2-methoxyphenoxy]propyl]-1H-1,2,3-triazol-1-yl]octyl]-1H-1,2,3-triazol-4-yl]propoxy]-3-methoxy-N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]benzamide
  参考文献：
  名称：

  Development of a Bivalent Dopamine D₂ Receptor Agonist

  摘要：

  Bivalent D-2 agonists may function as useful molecular probes for the discovery of novel neurological therapeutics. On the basis of our recently developed bivalent dopamine D-2 receptor antagonists of type 1, the bivalent agonist 2 was synthesized when a spacer built from 22 atoms was employed. Compared to the monovalent control compound 6 containing a capped spacer, the bis-aminoindane derivative 2 revealed substantial steepening of the competition curve, indicating a bivalent binding mode. Dimer-specific Hill slopes were not a result of varying functional properties because both the dopaminergic 2 and the monovalent control agent 6 proved to be D-2 agonists substantially inhibiting cAMP accumulation and inducing D-2 receptor internalization. Investigation of the heterobivalent ligands 8 and 9, containing an agonist and a phenylpiperazine-based antagonist pharmacophore, revealed moderate steepening of the displacement curves and antagonist to very weak partial agonist properties.

  DOI：

  10.1021/jm2009919
• 作为产物：
  描述：

  香草酸甲酯 在 TATU 、 potassium carbonate 、 N,N-二异丙基乙胺 、 potassium iodide 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.5h， 生成 3-methoxy-N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-4-(pent-4-yn-1-yloxy)benzamide
  参考文献：
  名称：

  Development of a Bivalent Dopamine D₂ Receptor Agonist

  摘要：

  Bivalent D-2 agonists may function as useful molecular probes for the discovery of novel neurological therapeutics. On the basis of our recently developed bivalent dopamine D-2 receptor antagonists of type 1, the bivalent agonist 2 was synthesized when a spacer built from 22 atoms was employed. Compared to the monovalent control compound 6 containing a capped spacer, the bis-aminoindane derivative 2 revealed substantial steepening of the competition curve, indicating a bivalent binding mode. Dimer-specific Hill slopes were not a result of varying functional properties because both the dopaminergic 2 and the monovalent control agent 6 proved to be D-2 agonists substantially inhibiting cAMP accumulation and inducing D-2 receptor internalization. Investigation of the heterobivalent ligands 8 and 9, containing an agonist and a phenylpiperazine-based antagonist pharmacophore, revealed moderate steepening of the displacement curves and antagonist to very weak partial agonist properties.

  DOI：

  10.1021/jm2009919