4,5,6,7-tetrahydro-3-acetylamino-4-oxobenzo(b)thiophene | 157981-76-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,5,6,7-tetrahydro-3-acetylamino-4-oxobenzo(b)thiophene
• 英文别名: N-(4-oxo-6,7-dihydro-5H-1-benzothiophen-3-yl)acetamide
• CAS: 157981-76-5
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: RQYPWAPYXTVEQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydro-3-acetylamino-4-oxobenzo(b)thiophene 、 乙醛酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以66%的产率得到5(4,5,6,7-tetrahydro-3-acetylaminobenzo(b)thiophene)-α-hydroxyacetic acid
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of thienocinnolin-3-(2H)-ones, bioisosters of antihypertensive and antithrombotic benzo(h)cinnolinones

  摘要：

  A number of thienocinnolin-3-(2H)-ones (2b, c; 3a, b) have been synthesized and tested for their pharmacological profile. These were compared with the bioisoster 8-acetylamino-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3-(2H)-one 1, which we reported to be a potent antihypertensive and antithrombotic agent. Binding studies on phosphodiesterase (PDE) isoenzymes indicate that the test compounds exhibited a modest affinity towards PDE III (2c, 3a, b) and PDE V (2b, c). In vivo tests indicated that only 3b displayed antihypertensive properties comparable to the model while all the new derivatives exhibited lower hypotensive activity. All compounds, with the exception of 2b, were more potent than 1 in inhibiting collagen-induced platelet aggregation. Molecular mechanics calculations were performed on compounds 2 and 3 which were compared with the model 1.

  DOI：

  10.1016/0223-5234(94)90072-8
• 作为产物：
  描述：

  2-bromo-6,7-dihydrobenzo[b]thiophen-4(5H)-one 在 硫酸 、 铁粉 、 铜 、 溶剂黄146 、 potassium nitrate 作用下， 以 丙酸 为溶剂， 反应 10.58h， 生成 4,5,6,7-tetrahydro-3-acetylamino-4-oxobenzo(b)thiophene
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of thienocinnolin-3-(2H)-ones, bioisosters of antihypertensive and antithrombotic benzo(h)cinnolinones

  摘要：

  A number of thienocinnolin-3-(2H)-ones (2b, c; 3a, b) have been synthesized and tested for their pharmacological profile. These were compared with the bioisoster 8-acetylamino-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3-(2H)-one 1, which we reported to be a potent antihypertensive and antithrombotic agent. Binding studies on phosphodiesterase (PDE) isoenzymes indicate that the test compounds exhibited a modest affinity towards PDE III (2c, 3a, b) and PDE V (2b, c). In vivo tests indicated that only 3b displayed antihypertensive properties comparable to the model while all the new derivatives exhibited lower hypotensive activity. All compounds, with the exception of 2b, were more potent than 1 in inhibiting collagen-induced platelet aggregation. Molecular mechanics calculations were performed on compounds 2 and 3 which were compared with the model 1.

  DOI：

  10.1016/0223-5234(94)90072-8