4,5,6,7-tetrahydro-2-acetylamino-7-oxobenzo(b)thiophene-6-malonic acid diethyl ester | 157981-84-5

• 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-2-acetylamino-7-oxobenzo(b)thiophene-6-malonic acid diethyl ester
• 英文别名: diethyl 2-(2-acetamido-7-oxo-5,6-dihydro-4H-1-benzothiophen-6-yl)propanedioate
• CAS: 157981-84-5
• 化学式: C₁₇H₂₁NO₆S
• 分子量: 367.423
• InChiKey: VKAPTCSTHRFFIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydro-2-acetylamino-7-oxobenzo(b)thiophene-6-malonic acid diethyl ester 在 sodium hydroxide 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 8-acetylamino-4,4a,5,6-tetrahydrothieno(2,3-h)cinnolin-3-(2H)-one
  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：

  5,6-二氢-1-苯并噻吩-7(4H)-酮 在 硫酸 、 溴 、 铁粉 、 sodium hydride 、 溶剂黄146 、 potassium nitrate 作用下， 以 乙醚 为溶剂， 反应 13.5h， 生成 4,5,6,7-tetrahydro-2-acetylamino-7-oxobenzo(b)thiophene-6-malonic acid diethyl ester
  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

文献信息

• Synthesis and pharmacological evaluation of thienocinnolin-3-(2H)-ones, bioisosters of antihypertensive and antithrombotic benzo(h)cinnolinones
  作者：GA Pinna、MM Curzu、G Cignarella、D Barlocco、M D'Amico、A Filippelli、V De Novellis、F Rossi

  DOI：10.1016/0223-5234(94)90072-8

  日期：1994.1

  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.