5-(2-Chloro-phenyl)-3-ethyl-7-[2-(4-isobutyl-phenyl)-ethyl]-1,3-dihydro-thieno[2,3-e][1,4]diazepine-2-thione | 183130-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 5-(2-Chloro-phenyl)-3-ethyl-7-[2-(4-isobutyl-phenyl)-ethyl]-1,3-dihydro-thieno[2,3-e][1,4]diazepine-2-thione
• 英文别名: 5-(2-Chlorophenyl)-3-ethyl-7-[2-[4-(2-methylpropyl)phenyl]ethyl]-1,3-dihydrothieno[2,3-e][1,4]diazepine-2-thione
• CAS: 183130-25-8
• 化学式: C₂₇H₂₉ClN₂S₂
• 分子量: 481.126
• InChiKey: QPXOZHHPNZQTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-Chloro-phenyl)-3-ethyl-7-[2-(4-isobutyl-phenyl)-ethyl]-1,3-dihydro-thieno[2,3-e][1,4]diazepine-2-thione 在 一水合肼 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 4-(2-Chloro-phenyl)-6-ethyl-2-[2-(4-isobutyl-phenyl)-ethyl]-9-methyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulene
  参考文献：
  名称：

  Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system

  摘要：

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.

  DOI：

  10.1016/0223-5234(96)85877-6
• 作为产物：
  描述：

  3-(4-异丁基苯甲酰基)丙酸 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 tetraphosphorus decasulfide 、 Celite 、 三氟化硼乙醚 、 sulfur 、 一水合肼 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 乙二醇 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 37.0h， 生成 5-(2-Chloro-phenyl)-3-ethyl-7-[2-(4-isobutyl-phenyl)-ethyl]-1,3-dihydro-thieno[2,3-e][1,4]diazepine-2-thione
  参考文献：
  名称：

  Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system

  摘要：

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.

  DOI：

  10.1016/0223-5234(96)85877-6