dimethyl 5,5'-(2,5,8,11,14-pentaoxapentadecane-1,15-diyl)bis(pyrazolo[1,5-a]pyridine-3-carboxylate) | 1355460-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: dimethyl 5,5'-(2,5,8,11,14-pentaoxapentadecane-1,15-diyl)bis(pyrazolo[1,5-a]pyridine-3-carboxylate)
• CAS: 1355460-28-4
• 化学式: C₂₈H₃₄N₄O₉
• 分子量: 570.599
• InChiKey: ULLLCVWKSFBNQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  41.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  133.35
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  dimethyl 5,5'-(2,5,8,11,14-pentaoxapentadecane-1,15-diyl)bis(pyrazolo[1,5-a]pyridine-3-carboxylate) 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 5,5'-(2,5,8,11,14-pentaoxapentadecane-1,15-diyl)bis[N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]pyrazolo[1,5-a]pyridine-3-carboxamide]
  参考文献：
  名称：

  Bivalent molecular probes for dopamine D2-like receptors

  摘要：

  Merging two arylamidoalkyl substituted phenylpiperazines as prototypical recognition elements for dopamine D-2-like receptors by oligoethylene glycol linkers led to a series of bivalent ligands. These dimers were investigated in comparison to their monomeric analogues for their dopamine D-2long, D-2short, D-3 and D-4 receptor binding. Radioligand binding experiments revealed strong bivalent effects for some para-substituted benzamide derivatives. For the D-3 subtype, the target compounds 32, 34 and 36 showed an up to 70-fold increase of affinity and a substantial enhancement of subtype selectivity when compared to the monovalent analogue 24. Analysis of the binding curves displayed Hill slopes very close to one indicating that the bivalent ligands displace 1 equiv of radioligand. Obviously, the two pharmacophores occupy an orthosteric and an allosteric binding site rather than adopting a receptor-bridging binding mode. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.063
• 作为产物：
  描述：

  methyl 5-(hydroxymethyl)pyrazolo[1,5-a]pyridine-3-carboxylate 在 三溴化磷 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 dimethyl 5,5'-(2,5,8,11,14-pentaoxapentadecane-1,15-diyl)bis(pyrazolo[1,5-a]pyridine-3-carboxylate)
  参考文献：
  名称：

  Bivalent molecular probes for dopamine D2-like receptors

  摘要：

  Merging two arylamidoalkyl substituted phenylpiperazines as prototypical recognition elements for dopamine D-2-like receptors by oligoethylene glycol linkers led to a series of bivalent ligands. These dimers were investigated in comparison to their monomeric analogues for their dopamine D-2long, D-2short, D-3 and D-4 receptor binding. Radioligand binding experiments revealed strong bivalent effects for some para-substituted benzamide derivatives. For the D-3 subtype, the target compounds 32, 34 and 36 showed an up to 70-fold increase of affinity and a substantial enhancement of subtype selectivity when compared to the monovalent analogue 24. Analysis of the binding curves displayed Hill slopes very close to one indicating that the bivalent ligands displace 1 equiv of radioligand. Obviously, the two pharmacophores occupy an orthosteric and an allosteric binding site rather than adopting a receptor-bridging binding mode. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.063