2-Chloro-5-prop-2-ynyl-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole | 131637-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-Chloro-5-prop-2-ynyl-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole
• CAS: 131637-25-7
• 化学式: C₁₆H₁₆ClN
• 分子量: 257.763
• InChiKey: WOSFCBQDEVWIPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(2-chlorophenyl)2-iodo-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine 、 2-Chloro-5-prop-2-ynyl-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole 在 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 2-Chloro-5-{3-[4-(2-chloro-phenyl)-9-methyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-2-yl]-prop-2-ynyl}-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole
  参考文献：
  名称：

  Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor

  摘要：

  A series of [1,2,4]triazolo[4,3-alpha][1,4]benzodiazepines bearing an ethynyl functionality at the 8-position and the isosteric thieno[3,2-f][1,2,4]triazolo[4,3-alpha][1,4]diazepines were prepared and evaluated as antagonists of platelet activating factor. The effects of substitution were explored in in vitro and in vivo test systems designed to measured PAF-antagonistic activity. Results are discussed and compared with previously published data. Many of the compounds had activity superior to WEB 2086, compound 1. In general, the thieno analogues exhibited better oral activity than the corresponding benzodiazepines. The duration of activity upon oral administration was modulated by the substitution on the acetylenic side chain. Compounds 71 and 81 were selected for further pharmacological evaluation as a result of their good oral potency and exceptionally long duration of action.

  DOI：

  10.1021/jm00107a048
• 作为产物：
  描述：

  2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole 、 3-溴丙炔 在 potassium tert-butylate 作用下， 生成 2-Chloro-5-prop-2-ynyl-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole
  参考文献：
  名称：

  Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor

  摘要：

  A series of [1,2,4]triazolo[4,3-alpha][1,4]benzodiazepines bearing an ethynyl functionality at the 8-position and the isosteric thieno[3,2-f][1,2,4]triazolo[4,3-alpha][1,4]diazepines were prepared and evaluated as antagonists of platelet activating factor. The effects of substitution were explored in in vitro and in vivo test systems designed to measured PAF-antagonistic activity. Results are discussed and compared with previously published data. Many of the compounds had activity superior to WEB 2086, compound 1. In general, the thieno analogues exhibited better oral activity than the corresponding benzodiazepines. The duration of activity upon oral administration was modulated by the substitution on the acetylenic side chain. Compounds 71 and 81 were selected for further pharmacological evaluation as a result of their good oral potency and exceptionally long duration of action.

  DOI：

  10.1021/jm00107a048