[2-Amino-5-bromo-4-[4-(trifluoromethyl)phenyl]thiophen-3-yl]-phenylmethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-Amino-5-bromo-4-[4-(trifluoromethyl)phenyl]thiophen-3-yl]-phenylmethanone
• 化学式: C₁₈H₁₁BrF₃NOS
• 分子量: 426.257
• InChiKey: HASMWTVLMNBFSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-4'-(三氟甲基)苯乙酮 、 苯甲酰乙腈 在 sulfur 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以52%的产率得到[2-Amino-5-bromo-4-[4-(trifluoromethyl)phenyl]thiophen-3-yl]-phenylmethanone
  参考文献：
  名称：

  2-Amino-3-benzoylthiophene Allosteric Enhancers of A₁ Adenosine Agonist Binding:  New 3, 4-, and 5-Modifications

  摘要：

  2-Amino-3-aroylthiophenes are agonist allosteric enhancers (AE) at the A, adenosine receptor (A(1)AR). Here we report the syntheses of three kinds of novel 2-aminothiophenes and assays of their AE activity at the human A(1)AR (hA(1)AR), namely, (1) 2-amino-4,5-diphenylthiophene-3-carboxylates, 3a-h, (2) 2-amino-3-benzoyl-4,5-diphenylthiophenes, 7a-p, and (3) 2-amino-5-bromo-3-benzoyl-4-phenylthiophenes, 10a-h. An in vitro assay employing the A(1)AR agonist [I-125]ABA and membranes from CHO-K1 cells stably expressing the hA(1)AR measured an index of AE activity, the ability of a candidate AE to stabilize the agonist-A(1)AR-G protein ternary complex, scored as the percentage of ternary complex remaining after 10 min of dissociation initiated by CPX and GTPgammaS. The AE activity score of 2-amino-4,5-dimethyl-3-(3-trifluoromethylbenzoyl)thiophene (PD 81,723), which was 19%, served as a standard for comparison. Two 3-carboxythiophene 3-trifluoromethylbenzyl esters, 3d (49%) and 3f (63%), had substantial AE activity. The 3-(1-naphthoyl) substituent of 7e (52%) also supported AE activity. Compounds in series 3 tended to be more potent, 10a and 10c having scores of 91 and 80%, respectively. The activity of 2-amino-5-bromo-3-ethoxycarbonyl-4-(3-nitrophenyl)thiophene, 10h (26%), is an exception to the rule that a 3-ethoxycarbonyl substituent cannot support AE activity.

  DOI：

  10.1021/jm020295m