6-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-thiazolo[3,2-b][1,2,4]triazole | 140405-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-thiazolo[3,2-b][1,2,4]triazole
• 英文别名: Thiazolo(3,2-b)(1,2,4)triazole, 6-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-；6-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-[1,3]thiazolo[3,2-b][1,2,4]triazole
• CAS: 140405-73-8
• 化学式: C₂₀H₁₉N₃O₄S
• 分子量: 397.455
• InChiKey: FBAACQZYUBAHQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(3,4,5-trimethoxyphenyl)-4H-5-mercapto-1,2,4-triazole 在 盐酸 、 甲醇 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 6-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-thiazolo[3,2-b][1,2,4]triazole
  参考文献：
  名称：

  Synthesis and biological evaluation of thiazolo-triazole derivatives

  摘要：

  Two series of isomeric thiazolo[3,2-b][1,2,4]triazole and thiazolo[2,3-c][1,2,4]triazole derivatives were prepared following multiple synthetic pathways. The obtained compounds were submitted to preliminar pharmacological assays to evaluate their anti-inflammatory, analgesic and antipyretic activity. Suggestions about structure-activity relationships between the two classes of isomers were delineated. Moreover, some of the starting molecules, phenacylthio[1,2,4]triazoles were submitted to microbiological analysis to test their antibacterial and antimycotic activity.

  DOI：

  10.1016/0223-5234(91)90135-a

文献信息

• Discovery of 6-aryl-2-(3,4,5-trimethoxyphenyl)thiazole[3,2-b][1,2,4]triazoles as potent tubulin polymerization inhibitors
  作者：Na Li、Qi Guan、Yilang Hong、Bowen Zhang、Mi Li、Xuewen Li、Bo Li、Lan Wu、Weige Zhang

  DOI：10.1016/j.ejmech.2023.115402

  日期：2023.8

  in the exploration of novel small molecules for oncotherapy. Based on the analysis of the binding models of tubulin and reported CBSIs, a series of 6-aryl-2-(3,4,5-trimethoxyphenyl)thiazole[3,2-b][1,2,4]triazoles were designed as potential tubulin polymerization inhibitors by binding to distinct colchicine domain of tubulin. Among the compounds synthesized, 7w not only shown noteworthy potency against

  微管蛋白/秋水仙碱结合位点抑制剂 (CBSI) 共晶结构在探索用于肿瘤治疗的新型小分子中发挥着重要作用。基于对微管蛋白结合模型的分析和已报道的 CBSI，设计了一系列 6-aryl-2-(3,4,5-trimethoxyphenyl)thiazole[3,2- b ][1,2,4]triazoles通过与微管蛋白的不同秋水仙碱结构域结合，作为潜在的微管蛋白聚合抑制剂。在合成的化合物中，7w不仅对 SGC-7901 癌细胞系 (IC 50  = 0.21 μM) 表现出显着的效力，而且在正常细胞系 (HUVEC) 中表现出比秋水仙碱更低的细胞毒性。机制研究表明7w可通过抑制微管蛋白聚合引发 G 2 /M 阻滞，从而引起癌细胞凋亡。在 4T1 异种移植小鼠模型中，7w在不减轻体重的情况下显着抑制肿瘤生长，证明了在秋水仙碱结合位点具有独特结合模式的进一步开发的潜力。