2-[5-bromo-4-methyl-3-(3-(trifluoromethyl)benzoyl)thiophen-2-yl]-isoindole-1,3-dione | 1355155-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[5-bromo-4-methyl-3-(3-(trifluoromethyl)benzoyl)thiophen-2-yl]-isoindole-1,3-dione
• CAS: 1355155-89-3
• 化学式: C₂₁H₁₁BrF₃NO₃S
• 分子量: 494.288
• InChiKey: PANDTXOEOSNUCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[5-bromo-4-methyl-3-(3-(trifluoromethyl)benzoyl)thiophen-2-yl]-isoindole-1,3-dione 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以1.6 g的产率得到2-[5-bromo-4-bromomethyl-3-(3-(trifluoromethyl)benzoyl)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
• 作为产物：
  描述：

  间三氟甲氧基苯甲酰乙腈 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 三乙胺 、 过氧化苯甲酰 作用下， 以 乙醇 、 苯 为溶剂， 反应 27.0h， 生成 2-[5-bromo-4-methyl-3-(3-(trifluoromethyl)benzoyl)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