4-(benzamido)butyl p-toluene sulfonate | 1355460-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(benzamido)butyl p-toluene sulfonate
• CAS: 1355460-63-7
• 化学式: C₁₈H₂₁NO₄S
• 分子量: 347.435
• InChiKey: ZQDCZYZHRSQWHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(benzamido)butyl p-toluene sulfonate 、 1,1'-[2,5,8,11,14-pentaoxapentadecane-1,15-diylbis(2-methoxy-4,1-phenylene)]dipiperazine 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以12%的产率得到N,N'-[2,5,8,11,14-pentaoxapentadecane-1,15-diylbis[(2-methoxy-4,1-phenylene)piperazine-4,1-diylbutane-4,1-diyl]]dibenzamide
  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：

  N-(4-hydroxybutyl)benzamide 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以53%的产率得到4-(benzamido)butyl p-toluene sulfonate
  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