11-Anilino-4,5-dimethyl-6-thia-1,8,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-3(7),4,8,10-tetraen-2-one | 1430813-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 11-Anilino-4,5-dimethyl-6-thia-1,8,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-3(7),4,8,10-tetraen-2-one
• 英文别名: 11-anilino-4,5-dimethyl-6-thia-1,8,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-3(7),4,8,10-tetraen-2-one
• CAS: 1430813-41-4
• 化学式: C₁₅H₁₃N₅OS
• 分子量: 311.367
• InChiKey: NBZLWOPGJUMXDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 4,5-dimethyl-2-(1H-tetrazol-1-yl)thiophene-3-carboxylate 在 一水合肼 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 11-Anilino-4,5-dimethyl-6-thia-1,8,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-3(7),4,8,10-tetraen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents

  摘要：

  A new series of thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a] pyrimidines was synthesized. The newly synthesized compounds were evaluated for their anti-inflammatory and analgesic activity using diclofenac Na as a reference standard. Additionally, the ulcerogenic effects and acute toxicity (ALD(50)) values of the active compounds were also determined. In general, the thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine derivatives exhibited better biological activities than the thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines. Collectively, the thienotriazolopyrimidine derivatives 9, 13 and 14a were proved to display distinctive anti-inflammatory activity at the acute and subacute models as well as good analgesic profile with a delayed onset of action. Moreover, they revealed good gastrointestinal safety profile and are well tolerated by experimental animals with high safety margin (ALD(50) > 0.3 g/kg). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.003

文献信息

• Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents
  作者：Hayam M. Ashour、Omaima G. Shaaban、Ola H. Rizk、Ibrahim M. El-Ashmawy

  DOI：10.1016/j.ejmech.2012.12.003

  日期：2013.4

  A new series of thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a] pyrimidines was synthesized. The newly synthesized compounds were evaluated for their anti-inflammatory and analgesic activity using diclofenac Na as a reference standard. Additionally, the ulcerogenic effects and acute toxicity (ALD(50)) values of the active compounds were also determined. In general, the thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine derivatives exhibited better biological activities than the thieno[2',3':4,5]pyrimido[1,2-b][1,2,4]triazines. Collectively, the thienotriazolopyrimidine derivatives 9, 13 and 14a were proved to display distinctive anti-inflammatory activity at the acute and subacute models as well as good analgesic profile with a delayed onset of action. Moreover, they revealed good gastrointestinal safety profile and are well tolerated by experimental animals with high safety margin (ALD(50) > 0.3 g/kg). (C) 2012 Elsevier Masson SAS. All rights reserved.