2-{5-bromo-3-(4-chlorobenzoyl)-4-[(4-(4-chlorobenzyl)piperazin-1-yl)methyl]thiophen-2-yl}-isoindole-1,3-dione | 1355156-61-4

• 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: 2-{5-bromo-3-(4-chlorobenzoyl)-4-[(4-(4-chlorobenzyl)piperazin-1-yl)methyl]thiophen-2-yl}-isoindole-1,3-dione
• CAS: 1355156-61-4
• 化学式: C₃₁H₂₄BrCl₂N₃O₃S
• 分子量: 669.426
• InChiKey: NECIAVGLBHTLTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.93
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-{5-bromo-3-(4-chlorobenzoyl)-4-[(4-(4-chlorobenzyl)piperazin-1-yl)methyl]thiophen-2-yl}-isoindole-1,3-dione 在 palladium 10% on activated carbon 、 氢气 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 6.0h， 生成 {2-氨基-4-[(4-(4-氯苄基)哌嗪-1-基)甲基]噻吩-3-基}(4-氯苯基)甲酮
  参考文献：
  名称：

  Structure–activity relationships of 2-amino-3-aroyl-4-[(4-arylpiperazin-1-yl)methyl]thiophenes. Part 2: Probing the influence of diverse substituents at the phenyl of the arylpiperazine moiety on allosteric enhancer activity at the A1 adenosine receptor

  摘要：

  In a preliminary article, we reported the potent allosteric enhancer activity at the AI adenosine receptor of a small series of 2-amino-3-(4-chlorobenzoyl)-4[4-(aryl)piperazin-1-yl)methyl]thiophene derivatives bearing electron-withdrawing or electron-releasing groups at the para-position of the phenylpiperazine moiety. In the present study, we report the development of the compounds previously studied by modifying both the number and position of substituents on the phenylpiperazine moiety, aimed at establishing a structure-activity relationship identifying additional compounds with improved activity.The nature and the position of substituents on the phenyl ring tethered to the piperazine seemed to exert a fundamental influence on the allosteric enhancer activity, with the 3,4-difluoro 4i, 3-chloro-4-fluoro 4o, and 4-trifluoromethoxy 4ak derivatives being the most active compounds in binding (saturation and competition experiments) and functional cAMP studies. This study shows that it is also possible to obtain a good separation between allosteric enhancement and antagonistic activity at the A(1) adenosine receptor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.044
• 作为产物：
  描述：

  1-(4-氯苄基)哌嗪 、 2-[5-bromo-4-bromomethyl-3-(4-chloro-benzoyl)-thiophen-2-yl]-isoindole-1,3-dione 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以43%的产率得到2-{5-bromo-3-(4-chlorobenzoyl)-4-[(4-(4-chlorobenzyl)piperazin-1-yl)methyl]thiophen-2-yl}-isoindole-1,3-dione
  参考文献：
  名称：

  Structure–activity relationships of 2-amino-3-aroyl-4-[(4-arylpiperazin-1-yl)methyl]thiophenes. Part 2: Probing the influence of diverse substituents at the phenyl of the arylpiperazine moiety on allosteric enhancer activity at the A1 adenosine receptor

  摘要：

  In a preliminary article, we reported the potent allosteric enhancer activity at the AI adenosine receptor of a small series of 2-amino-3-(4-chlorobenzoyl)-4[4-(aryl)piperazin-1-yl)methyl]thiophene derivatives bearing electron-withdrawing or electron-releasing groups at the para-position of the phenylpiperazine moiety. In the present study, we report the development of the compounds previously studied by modifying both the number and position of substituents on the phenylpiperazine moiety, aimed at establishing a structure-activity relationship identifying additional compounds with improved activity.The nature and the position of substituents on the phenyl ring tethered to the piperazine seemed to exert a fundamental influence on the allosteric enhancer activity, with the 3,4-difluoro 4i, 3-chloro-4-fluoro 4o, and 4-trifluoromethoxy 4ak derivatives being the most active compounds in binding (saturation and competition experiments) and functional cAMP studies. This study shows that it is also possible to obtain a good separation between allosteric enhancement and antagonistic activity at the A(1) adenosine receptor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.044