1-(3,4,5-trimethoxyphenyl)-5-p-tolyl-1H-1,2,4-triazole | 1226898-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3,4,5-trimethoxyphenyl)-5-p-tolyl-1H-1,2,4-triazole
• 英文别名: 5-(4-Methylphenyl)-1-(3,4,5-trimethoxyphenyl)-1,2,4-triazole
• CAS: 1226898-08-3
• 化学式: C₁₈H₁₉N₃O₃
• 分子量: 325.367
• InChiKey: QKUOHEFWHQIIDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-bromo-1-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole 、 4-甲苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以55%的产率得到1-(3,4,5-trimethoxyphenyl)-5-p-tolyl-1H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis and Antitumor Activity of 1,5-Disubstituted 1,2,4-Triazoles as Cis-Restricted Combretastatin Analogues

  摘要：

  A series of 1-aryl-5-(3',4',5'-trimethoxyphenyl) derivatives and their related 1-(3',4',5'-trimethoxyphenyl)5-aryl-1,2,4-triazoles, designed as cis-restricted combretastatin analogues, were synthesized and evaluated for antiproliferative activity, inhibitory effects on tubulin polymerization, cell cycle effects, and apoptosis induction. Their activity was greater than, or comparable with, that of the reference compound CA-4. Flow cytometry studies showed that HeLa and Jurkat cells treated with the most active compounds 4l and 4o were arrested in the G2/M phase of the cell cycle in a concentration dependent manner. This effect was accompanied by apoptosis of the cells, mitochondrial depolarization, generation of reactive oxygen species, activation of caspase-3, and PA RP cleavage. Compound 41 was also shown to have potential antivascular activity, since it induced endothelial cell shape change in vitro and disrupted the sprouting of endothelial cells in the chick aortic ring assay.

  DOI：

  10.1021/jm100245q

文献信息

• Synthesis and Antitumor Activity of 1,5-Disubstituted 1,2,4-Triazoles as Cis-Restricted Combretastatin Analogues
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Olga Cruz-Lopez、Carlota Lopez Cara、Maria Dora Carrion、Andrea Brancale、Ernest Hamel、Longchuan Chen、Roberta Bortolozzi、Giuseppe Basso、Giampietro Viola

  DOI：10.1021/jm100245q

  日期：2010.5.27

  A series of 1-aryl-5-(3',4',5'-trimethoxyphenyl) derivatives and their related 1-(3',4',5'-trimethoxyphenyl)5-aryl-1,2,4-triazoles, designed as cis-restricted combretastatin analogues, were synthesized and evaluated for antiproliferative activity, inhibitory effects on tubulin polymerization, cell cycle effects, and apoptosis induction. Their activity was greater than, or comparable with, that of the reference compound CA-4. Flow cytometry studies showed that HeLa and Jurkat cells treated with the most active compounds 4l and 4o were arrested in the G2/M phase of the cell cycle in a concentration dependent manner. This effect was accompanied by apoptosis of the cells, mitochondrial depolarization, generation of reactive oxygen species, activation of caspase-3, and PA RP cleavage. Compound 41 was also shown to have potential antivascular activity, since it induced endothelial cell shape change in vitro and disrupted the sprouting of endothelial cells in the chick aortic ring assay.