8-Acetyl-5-oxo-5,6-dihydro-4H-1,2,6,10b-tetraaza-benzo[e]azulene-3-carboxylic acid ethyl ester | 210989-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并二氮卓类
• 英文名称: 8-Acetyl-5-oxo-5,6-dihydro-4H-1,2,6,10b-tetraaza-benzo[e]azulene-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 8-acetyl-5-oxo-4,6-dihydrotriazolo[1,5-a][1,5]benzodiazepine-3-carboxylate
• CAS: 210989-50-7
• 化学式: C₁₅H₁₄N₄O₄
• 分子量: 314.301
• InChiKey: IQKGRQWGKXKFNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-Acetyl-5-oxo-5,6-dihydro-4H-1,2,6,10b-tetraaza-benzo[e]azulene-3-carboxylic acid ethyl ester 、 碘甲烷 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到8-Acetyl-6-methyl-5-oxo-5,6-dihydro-4H-1,2,6,10b-tetraaza-benzo[e]azulene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a][1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding

  摘要：

  This paper reports the synthesis of new 1,2,3-triazolo[1,4]benzodiazepine and 1,2,3-triazolo[1,5]benzodiazepine derivatives and their evaluation toward benzodiazepine receptors, Receptor affinity gradually and remarkably increases by moving the nitrogen atom of the central ring from position 3 through 4 to position 5, to give the most effective compound 6a (K-i = 150 nM). N-methylation of the diazepine ring (7a) lowers receptorial binding. Introduction of a chlorine atom on the benzene ring doubles the K-i value (6b) which remains unaltered by the N-methylation (7b). (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00025-1
• 作为产物：
  描述：

  1-(4-叠氮基-3-硝基苯基)乙酮 在 乙酰基丙二酸二乙酯 、 硫酸 、 水 、 sodium ethanolate 、 三氯化铁 、 铁粉 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 8-Acetyl-5-oxo-5,6-dihydro-4H-1,2,6,10b-tetraaza-benzo[e]azulene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a][1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding

  摘要：

  This paper reports the synthesis of new 1,2,3-triazolo[1,4]benzodiazepine and 1,2,3-triazolo[1,5]benzodiazepine derivatives and their evaluation toward benzodiazepine receptors, Receptor affinity gradually and remarkably increases by moving the nitrogen atom of the central ring from position 3 through 4 to position 5, to give the most effective compound 6a (K-i = 150 nM). N-methylation of the diazepine ring (7a) lowers receptorial binding. Introduction of a chlorine atom on the benzene ring doubles the K-i value (6b) which remains unaltered by the N-methylation (7b). (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00025-1