5,6-diphenyl-3--1,2,4-triazine | 171773-55-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,6-diphenyl-3--1,2,4-triazine
• 英文别名: 3-[(5,6-Diphenyl-1,2,4-triazin-3-yl)sulfanyl]propanoic acid
• CAS: 171773-55-0
• 化学式: C₁₈H₁₅N₃O₂S
• 分子量: 337.402
• InChiKey: YUGLDJHKLOBIPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-二氨基萘 、 5,6-diphenyl-3--1,2,4-triazine 在 PPA 作用下， 反应 8.0h， 生成 2-[2-[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfanyl]ethyl]-1H-benzo[f]benzimidazole
  参考文献：
  名称：

  Bhalla; Srivastava; Bhalla, Bollettino Chimico Farmaceutico, 1995, vol. 134, # 1, p. 9 - 15

  摘要：

  DOI：
• 作为产物：
  描述：

  联苯甲酰 在 溶剂黄146 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成 5,6-diphenyl-3--1,2,4-triazine
  参考文献：
  名称：

  Discovery of 5,6-diaryl-1,2,4-triazines hybrids as potential apoptosis inducers

  摘要：

  A series of 5,6-diaryl-1,2,4-triazines hybrids bearing a 1,2,3-triazole linker were synthesized by molecular hybridization strategy and evaluated for antiproliferative activity against three selected cancer cell lines (MGC-803, EC-109 and PC-3). The first structure-activity relationship (SAR) for these 5,6-diaryl-1,2,4-triazines is explored in this report with evaluation of 15 variants of the structural class. Among these chemical derivatives, 3-(((1-(4-fluorobenzy1)-1H-1,2,3-triazol-4-yl)methyl)thio)-5,6-dipheny1-1,2,4-triazine(11E) showed the more potent inhibitory effect against three cell lines than 5-Fu. Cellular mechanism studies in MGC-803 cells elucidated 11E inhibited colony formation and arrested cell cycle at G2/M phase. Furthermore, compound 11E caused morphological changes, decreased mitochondrial membrane potential, and induced apoptosis through the apoptosis-related proteins in MGC-803 cells. It was the first time, to our knowledge, that 5,6-diaryl-1,2,4-triazines bearing a 1,2,3-triazole linker were used as potential apoptosis inducers. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.07.011

文献信息

• Bhalla; Srivastava; Bhalla, Bollettino Chimico Farmaceutico, 1995, vol. 134, # 1, p. 9 - 15
  作者：Bhalla、Srivastava、Bhalla、Shanker

  DOI：——

  日期：——
• Discovery of 5,6-diaryl-1,2,4-triazines hybrids as potential apoptosis inducers
  作者：Dong-Jun Fu、Jian Song、Yu-Hui Hou、Ruo-Han Zhao、Jia-Huan Li、Ruo-Wang Mao、Jia-Jia Yang、Ping Li、Xiao-Lin Zi、Zhong-Hua Li、Qing-Qing Zhang、Fei-Yan Wang、Sai-Yang Zhang、Yan-Bing Zhang、Hong-Min Liu

  DOI：10.1016/j.ejmech.2017.07.011

  日期：2017.9

  A series of 5,6-diaryl-1,2,4-triazines hybrids bearing a 1,2,3-triazole linker were synthesized by molecular hybridization strategy and evaluated for antiproliferative activity against three selected cancer cell lines (MGC-803, EC-109 and PC-3). The first structure-activity relationship (SAR) for these 5,6-diaryl-1,2,4-triazines is explored in this report with evaluation of 15 variants of the structural class. Among these chemical derivatives, 3-(((1-(4-fluorobenzy1)-1H-1,2,3-triazol-4-yl)methyl)thio)-5,6-dipheny1-1,2,4-triazine(11E) showed the more potent inhibitory effect against three cell lines than 5-Fu. Cellular mechanism studies in MGC-803 cells elucidated 11E inhibited colony formation and arrested cell cycle at G2/M phase. Furthermore, compound 11E caused morphological changes, decreased mitochondrial membrane potential, and induced apoptosis through the apoptosis-related proteins in MGC-803 cells. It was the first time, to our knowledge, that 5,6-diaryl-1,2,4-triazines bearing a 1,2,3-triazole linker were used as potential apoptosis inducers. (C) 2017 Elsevier Masson SAS. All rights reserved.