13-(4-Bromophenyl)-5-thia-13,14-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2(6),3-trien-12-one | 195433-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七噻吩
• 英文名称: 13-(4-Bromophenyl)-5-thia-13,14-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2(6),3-trien-12-one
• CAS: 195433-94-4
• 化学式: C₁₇H₁₅BrN₂OS
• 分子量: 375.289
• InChiKey: RVSQSNVXFHUTNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13-(4-Bromophenyl)-5-thia-13,14-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2(6),3-trien-12-one 在 氢溴酸 、 二甲基亚砜 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 以65%的产率得到13-(4-Bromophenyl)-5-thia-13,14-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2(6),3,10-tetraen-12-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：

  5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one 在 盐酸 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 18.5h， 生成 13-(4-Bromophenyl)-5-thia-13,14-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2(6),3-trien-12-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.