[2-amino-5-(2,2-dimethylpropyl)thiophen-3-yl](4-chlorophenyl)methanone | 1529777-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-amino-5-(2,2-dimethylpropyl)thiophen-3-yl](4-chlorophenyl)methanone
• 英文别名: (2-amino-4-neopentylthiophen-3-yl)(4-chlorophenyl)methanone；2-Amino-3-(4-chlorobenzoyl)-4-neopentylthiophene；[2-amino-4-(2,2-dimethylpropyl)thiophen-3-yl]-(4-chlorophenyl)methanone
• CAS: 1529777-61-4
• 化学式: C₁₆H₁₈ClNOS
• 分子量: 307.844
• InChiKey: IVOYQGMHPBIQFF-UHFFFAOYSA-N

物化性质

• 沸点：
  480.6±45.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-amino-5-(2,2-dimethylpropyl)thiophen-3-yl](4-chlorophenyl)methanone 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 14.5h， 生成 2-[3-(4-chlorobenzoyl)-5-(2,6-difluorophenyl)-4-(2,2-dimethylpropyl)-thiophen-2-yl]isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-amino-3-aroyl-4-neopentyl-5-substituted thiophene derivatives as allosteric enhancers of the A1 adenosine receptor

  摘要：

  2-Amino-3-benzoyl thiophenes have been widely reported to act as allosteric enhancers at the A(1) adenosine receptor. Their activity can be increased considerably by appropriate substitutions at the 4- and 5-positions of the thiophene ring. Substituent size at the thiophene C-4 position seemed to be a factor closely related to activity, with the 4-neopentyl (2,2-dimethylpropyl) substitution showing the greatest enhanced activity. A wide series of 2-amino-3-aroyl-4-neopentylthiophene derivatives with general structure 3, characterized by the presence of different substituents (bromine, aryl and heteroaryl) at the 5-position of the thiophene ring, have been identified as potent AEs at the A(1)AR. With only one exception, all of the synthesized compounds proved to be superior to the reference compound PD 81,723 in a functional assay. Derivatives 3p, 3u, 3am, 3ap and 3ar were the most active compounds in binding (saturation and competition) and functional cAMP studies, being able to potentiate agonist [H-3]CCPA binding to the A(1) receptor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.043
• 作为产物：
  描述：

  对氯苯乙酰腈 在 sulfur 、 溶剂黄146 、 三乙胺 、 β-丙氨酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 [2-amino-5-(2,2-dimethylpropyl)thiophen-3-yl](4-chlorophenyl)methanone
  参考文献：
  名称：

  2-Amino-5-arylethynyl-thiophen-3-yl-(phenyl)methanones as A₁ Adenosine Receptor Positive Allosteric Modulators

  摘要：

  DOI：

  10.1021/acsmedchemlett.3c00315

文献信息

• Synthesis and biological evaluation of novel 2-amino-3-aroyl-4-neopentyl-5-substituted thiophene derivatives as allosteric enhancers of the A1 adenosine receptor
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Olga Cruz-Lopez、Carlota Lopez Cara、Giulia Saponaro、Delia Preti、Mojgan Aghazadeh Tabrizi、Stefania Baraldi、Allan R. Moorman、Fabrizio Vincenzi、Pier Andrea Borea、Katia Varani

  DOI：10.1016/j.bmc.2013.11.043

  日期：2014.1

  2-Amino-3-benzoyl thiophenes have been widely reported to act as allosteric enhancers at the A(1) adenosine receptor. Their activity can be increased considerably by appropriate substitutions at the 4- and 5-positions of the thiophene ring. Substituent size at the thiophene C-4 position seemed to be a factor closely related to activity, with the 4-neopentyl (2,2-dimethylpropyl) substitution showing the greatest enhanced activity. A wide series of 2-amino-3-aroyl-4-neopentylthiophene derivatives with general structure 3, characterized by the presence of different substituents (bromine, aryl and heteroaryl) at the 5-position of the thiophene ring, have been identified as potent AEs at the A(1)AR. With only one exception, all of the synthesized compounds proved to be superior to the reference compound PD 81,723 in a functional assay. Derivatives 3p, 3u, 3am, 3ap and 3ar were the most active compounds in binding (saturation and competition) and functional cAMP studies, being able to potentiate agonist [H-3]CCPA binding to the A(1) receptor. (C) 2013 Elsevier Ltd. All rights reserved.