2-{5-bromo-3-(4-chlorobenzoyl)-4-[(4-(4-chloro-3-(trifluoromethyl)phenyl)piperazin-1-yl)methyl]thiophen-2-yl}-isoindole-1,3-dione | 1355156-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{5-bromo-3-(4-chlorobenzoyl)-4-[(4-(4-chloro-3-(trifluoromethyl)phenyl)piperazin-1-yl)methyl]thiophen-2-yl}-isoindole-1,3-dione
• CAS: 1355156-88-5
• 化学式: C₃₁H₂₁BrCl₂F₃N₃O₃S
• 分子量: 723.397
• InChiKey: RYLAXMRFUHSAQY-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  2-{5-bromo-3-(4-chlorobenzoyl)-4-[(4-(4-chloro-3-(trifluoromethyl)phenyl)piperazin-1-yl)methyl]thiophen-2-yl}-isoindole-1,3-dione 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以72%的产率得到2-{3-(4-chlorobenzoyl)-5-(2-phenylethynyl)-4-[(4-(4-chloro-3-(trifluoromethyl)phenyl)piperazin-1-yl)methyl]thiophen-2-yl}isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Allosteric Enhancers of the A₁ Adenosine Receptor Based on 2-Amino-3-(4′-Chlorobenzoyl)-4-Substituted-5-Arylethynyl Thiophene

  摘要：

  A Sonogashira coupling strategy was employed to synthesize a new series of allosteric modulators for the A(1) adenosine receptor based on the 2-amino-3-(p-chlorobenzoyl)-4-substituted thiophene skeleton, with a two-carbon (rigid or flexible) linker between the S-position of the thiophene ring and a (hetero)aryl or alkyl moiety. Among the compounds characterized by the presence of a common phenylacetylene moiety at the S-position of the thiophene ring, the neopentyl substitution at the 4-position supported a strong activity. In the series of 4-neopentyl derivatives, the presence of an acetylene spacer at the S-position of the thiophene is optimal for activity, whereas reduction of the acetylene to an ethyl moiety decreased activity, both in functional and binding assays. Derivatives 4e, 4g-h, 4j, 4l, and 4m were the most promising compounds in binding (saturation and competition) and functional cAMP studies, being able to potentiate agonist [H-3]CCPA binding to the A(1) receptor, with 4e as the best compound of the series. The latter compound also retarded the dissociation of another radiolabeled agonist, [H-3]NECA, from the receptor.

  DOI：

  10.1021/jm5008853