2-(4-chlorophenyl)-9-methyl-2,4,4a,5,6,7-hexahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one | 129477-43-6

• 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: 2-(4-chlorophenyl)-9-methyl-2,4,4a,5,6,7-hexahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one
• 英文别名: 13-(4-chlorophenyl)-4-methyl-5-thia-13,14-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2(6),3-trien-12-one
• CAS: 129477-43-6
• 化学式: C₁₈H₁₇ClN₂OS
• 分子量: 344.865
• InChiKey: LWMZJZISZFCXBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-(4-chlorophenyl)-9-methyl-2,4,4a,5,6,7-hexahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 2-(4-chlorophenyl)-2,5,6,7-tetrahydro-9-methyl-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one
  参考文献：
  名称：

  Thienocycloheptapyridazine compounds and their pharmaceutical use

  摘要：

  一种噻吩环庚吡嗪化合物，其化学式为##STR1##其中R代表氢、卤素或C.sub.1-4烷基，Ar代表芳基、杂芳基或带有至少一个卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、硝基、氨基、羟基、三氟甲基和/或C.sub.2-5烷酰胺基的芳基或杂芳基；4位和42位之间的键代表单键或双键。该化合物可用作抗焦虑剂、治疗遗忘症药物、脑功能激活药物或抗痴呆药物。

  公开号：

  US05153194A1
• 作为产物：
  描述：

  2-methyl-5,6,7,8-tetrahydro-5-cyanomethyl-4H-cyclohepta[b]thiophen-4-one 在 盐酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 2-(4-chlorophenyl)-9-methyl-2,4,4a,5,6,7-hexahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-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

• Thienocycloheptapyridazine compounds and their pharmaceutical use
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US05153194A1

  公开（公告）日：1992-10-06

  A thienocycloheptapyridazine compound of the formula ##STR1## wherein R stands for hydrogen, a halogen or a C.sub.1-4 alkyl, Ar stands for an aryl, a heteroaryl, or an aryl or a heteroaryl having as a substituent at least a halogen, a C.sub.1-4 alkyl, a C.sub.1-4 alkoxy, nitro, amino, hydroxy, trifluoromethyl and/or a C.sub.2-5 alkanoylamino; and the bond between 4-position and 42-position represents a single bond or a double bond, which is useful as an antianxiety agent, amnesia-treating drug, a brain function-activating drug or an antidementiac drug.

  一种噻吩环庚吡嗪化合物，其化学式为##STR1##其中R代表氢、卤素或C.sub.1-4烷基，Ar代表芳基、杂芳基或带有至少一个卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、硝基、氨基、羟基、三氟甲基和/或C.sub.2-5烷酰胺基的芳基或杂芳基；4位和42位之间的键代表单键或双键。该化合物可用作抗焦虑剂、治疗遗忘症药物、脑功能激活药物或抗痴呆药物。
• US5153194A
  申请人：——

  公开号：US5153194A

  公开（公告）日：1992-10-06
• 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.