8-Acetyl-2-(4-chloro-phenyl)-5,6-dihydro-2H-thieno[2,3-h]cinnolin-3-one | 195433-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-Acetyl-2-(4-chloro-phenyl)-5,6-dihydro-2H-thieno[2,3-h]cinnolin-3-one
• 英文别名: 8-Acetyl-2-(4-chlorophenyl)-5,6-dihydrothieno[2,3-h]cinnolin-3-one
• CAS: 195433-90-0
• 化学式: C₁₈H₁₃ClN₂O₂S
• 分子量: 356.832
• InChiKey: RUHQRVZZPSWIGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-Acetyl-2-(4-chloro-phenyl)-5,6-dihydro-2H-thieno[2,3-h]cinnolin-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.0h， 以81%的产率得到2-(4-Chloro-phenyl)-8-(1-hydroxy-ethyl)-5,6-dihydro-2H-thieno[2,3-h]cinnolin-3-one
  参考文献：
  名称：

  Synthesis and evaluation of novel 2-aryl-2,5,6,7-tetrahydro-3H-thieno [2′,3′:6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5, 6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones as anxiolytics

  摘要：

  A series of 2-aryl-2,5,6,7-tetrahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones were synthesized and evaluated for their affinity to benzodiazepine receptors (BZRs) in the excised brain of rats and also for their intrinsic efficacy in augmentation of the gamma-aminobutyric acid-induced chloride currents in the dissociated sensory neurons of frogs. The synthesized compounds showed a high affinity to BZRs. In these compounds, the substituents at the 2-position and at either the 8- or the 9-position and the ring size of the condensed ring affected the biological activity of the compounds. Thus, an introduction of 4-methyl- or 4-chloro-substitute phenyl ring into the 2-position, an introduction of methyl or ethyl into either the 8- or the 9-position, and an expansion of the 6-membered condensed ring to a 7-membered ring brought about a continuous shift of compounds from inverse to full agonists. Among the synthesized compounds, 8-(1 hydroxyethyl)-2-(4-methylphenyl)-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-one which can be classified as a BZR partial agonist, was found to exhibit an anxio-selective feature.

  DOI：

  10.1016/s0223-5234(97)83286-2
• 作为产物：
  描述：

  2-(4-chlorophenyl)-4,4a,5,6-tetrahydrothieno-[2,3-h]cinnolin-3(2H)-one 在 三氯化铝 、 氢溴酸 、 二甲基亚砜 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 8-Acetyl-2-(4-chloro-phenyl)-5,6-dihydro-2H-thieno[2,3-h]cinnolin-3-one
  参考文献：
  名称：

  Synthesis and evaluation of novel 2-aryl-2,5,6,7-tetrahydro-3H-thieno [2′,3′:6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5, 6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones as anxiolytics

  摘要：

  A series of 2-aryl-2,5,6,7-tetrahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones were synthesized and evaluated for their affinity to benzodiazepine receptors (BZRs) in the excised brain of rats and also for their intrinsic efficacy in augmentation of the gamma-aminobutyric acid-induced chloride currents in the dissociated sensory neurons of frogs. The synthesized compounds showed a high affinity to BZRs. In these compounds, the substituents at the 2-position and at either the 8- or the 9-position and the ring size of the condensed ring affected the biological activity of the compounds. Thus, an introduction of 4-methyl- or 4-chloro-substitute phenyl ring into the 2-position, an introduction of methyl or ethyl into either the 8- or the 9-position, and an expansion of the 6-membered condensed ring to a 7-membered ring brought about a continuous shift of compounds from inverse to full agonists. Among the synthesized compounds, 8-(1 hydroxyethyl)-2-(4-methylphenyl)-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-one which can be classified as a BZR partial agonist, was found to exhibit an anxio-selective feature.

  DOI：

  10.1016/s0223-5234(97)83286-2

文献信息

• Synthesis and evaluation of novel 2-aryl-2,5,6,7-tetrahydro-3H-thieno [2′,3′:6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5, 6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones as anxiolytics
  作者：H Tanaka、S Kirihara、H Yasumatsu、T Yakushiji、T Nakao

  DOI：10.1016/s0223-5234(97)83286-2

  日期：1997.7

  A series of 2-aryl-2,5,6,7-tetrahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones were synthesized and evaluated for their affinity to benzodiazepine receptors (BZRs) in the excised brain of rats and also for their intrinsic efficacy in augmentation of the gamma-aminobutyric acid-induced chloride currents in the dissociated sensory neurons of frogs. The synthesized compounds showed a high affinity to BZRs. In these compounds, the substituents at the 2-position and at either the 8- or the 9-position and the ring size of the condensed ring affected the biological activity of the compounds. Thus, an introduction of 4-methyl- or 4-chloro-substitute phenyl ring into the 2-position, an introduction of methyl or ethyl into either the 8- or the 9-position, and an expansion of the 6-membered condensed ring to a 7-membered ring brought about a continuous shift of compounds from inverse to full agonists. Among the synthesized compounds, 8-(1 hydroxyethyl)-2-(4-methylphenyl)-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-one which can be classified as a BZR partial agonist, was found to exhibit an anxio-selective feature.