1-(3,4,5-trimethoxyphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinazolin-5-one

• 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)-4-methyl-[1,2,4]triazolo[4,3-a]quinazolin-5-one
• 英文别名: 4-Methyl-1-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5-one；4-methyl-1-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5-one
• 化学式: C₁₉H₁₈N₄O₄
• 分子量: 366.376
• InChiKey: ANEBNUZSWWMZDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-异硫氰基苯甲酸甲酯 在 iron(III) chloride 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 36.0h， 生成 1-(3,4,5-trimethoxyphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinazolin-5-one
  参考文献：
  名称：

  Synthesis of triazoloquinazolinone based compounds as tubulin polymerization inhibitors and vascular disrupting agents

  摘要：

  A series of 1-phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5-ones designed as conformationally restricted CA 4 analogues, were tested for their tubulin polymerization and growth inhibitory activities. The 3-hydroxy-4-methoxy derivatives 11d and 12d are potent inhibitors of tubulin assembly but only the N-methylated amid counterpart 12d possesses potent anticancer activity in a large panel of cancer cell lines. Upon treatment with compound 12d, remarkable cell shape changes as cell migration and tube formation were elicited in HUVECs, consistent with vasculature damaging activity. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.056