5-amino-6,8-dicyano-7-[4-(4-morpholinyl)phenyl]-1-(prop-2-en-1-yl)-1H-[1,2,4]triazolo[1,5-a]pyridin-4-ium-2-thiolate | 1369588-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 5-amino-6,8-dicyano-7-[4-(4-morpholinyl)phenyl]-1-(prop-2-en-1-yl)-1H-[1,2,4]triazolo[1,5-a]pyridin-4-ium-2-thiolate
• 英文别名: 5-imino-7-(4-morpholin-4-ylphenyl)-1-prop-2-enyl-2-sulfanylidene-3H-[1,2,4]triazolo[1,5-a]pyridine-6,8-dicarbonitrile
• CAS: 1369588-80-6
• 化学式: C₂₁H₁₉N₇OS
• 分子量: 417.494
• InChiKey: PFGAENSDIYGVBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  <4-(1-Morpholinyl)benzylidene>malononitrile 、 N-Allyl-2-(2-cyanoacetyl)hydrazine-1-carbothioamide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以53%的产率得到5-amino-6,8-dicyano-7-[4-(4-morpholinyl)phenyl]-1-(prop-2-en-1-yl)-1H-[1,2,4]triazolo[1,5-a]pyridin-4-ium-2-thiolate
  参考文献：
  名称：

  Synthesis of [1,2,4]triazolo[1,5-a]pyridines of potential PGE2 inhibitory properties

  摘要：

  A variety of 5-amino-6,8-dicyano-1H-[1,2,4]triazolo[1,5-a]pyridin-4-ium-2-thiolate containing compounds 3a-i, 5a-c were prepared via reaction of arylidenemalononitriles la-c, 4a and 4b with 2[(substituted amino)thiocarbonyl]cyanoacetohydrazides 2a-d in refluxing ethanol in the presence of triethylamine. Anti-inflammatory activity screening of the synthesized compounds (at a dose of 50 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method in rats exhibited that the prepared heterocycles possess considerable pharmacological properties especially, 3f, 3h, 5b and 5c which reveal remarkable activities relative to indomethacin (which was used as a reference standard at a dose of 10 mg/kg body weight). PGE(2) inhibitory properties of the highly promising synthesized anti-inflammatory active agents (3f, 3h, 5b and 5c) were determined by PGE2 assay kit technique, which reveal remarkable activity coinciding greatly with the observed anti-inflammatory properties. Anti-tumor activity screening of 3b and 3e, as representative examples of the synthesized compounds, at a dose of 10 mu M utilizing 59 different human tumor cell lines, representing leukemia, melanoma and cancers of the lung, colon, brain, ovary, breast, prostate and kidney exhibited that the tested compounds reflect mild or no activity at all against most of the used human tumor cell lines. However, compound 3e reveals considerable anti-tumor properties against leukemia CCRF-CEM and HL-60(TB) cell line. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.09.049

文献信息

• Synthesis of [1,2,4]triazolo[1,5-a]pyridines of potential PGE2 inhibitory properties
  作者：Adel S. Girgis、Flora F. Barsoum

  DOI：10.1016/j.ejmech.2008.09.049

  日期：2009.5

  A variety of 5-amino-6,8-dicyano-1H-[1,2,4]triazolo[1,5-a]pyridin-4-ium-2-thiolate containing compounds 3a-i, 5a-c were prepared via reaction of arylidenemalononitriles la-c, 4a and 4b with 2[(substituted amino)thiocarbonyl]cyanoacetohydrazides 2a-d in refluxing ethanol in the presence of triethylamine. Anti-inflammatory activity screening of the synthesized compounds (at a dose of 50 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method in rats exhibited that the prepared heterocycles possess considerable pharmacological properties especially, 3f, 3h, 5b and 5c which reveal remarkable activities relative to indomethacin (which was used as a reference standard at a dose of 10 mg/kg body weight). PGE(2) inhibitory properties of the highly promising synthesized anti-inflammatory active agents (3f, 3h, 5b and 5c) were determined by PGE2 assay kit technique, which reveal remarkable activity coinciding greatly with the observed anti-inflammatory properties. Anti-tumor activity screening of 3b and 3e, as representative examples of the synthesized compounds, at a dose of 10 mu M utilizing 59 different human tumor cell lines, representing leukemia, melanoma and cancers of the lung, colon, brain, ovary, breast, prostate and kidney exhibited that the tested compounds reflect mild or no activity at all against most of the used human tumor cell lines. However, compound 3e reveals considerable anti-tumor properties against leukemia CCRF-CEM and HL-60(TB) cell line. (C) 2008 Elsevier Masson SAS. All rights reserved.