6-[(E)-2-(furan-2-yl)ethenyl]-4-[(E)(4-nitrobenzylidene)amino]-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one | 1396681-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-[(E)-2-(furan-2-yl)ethenyl]-4-[(E)(4-nitrobenzylidene)amino]-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one
• 英文别名: 6-[(E)-2-(furan-2-yl)ethenyl]-4-[(E)-(4-nitrophenyl)methylideneamino]-3-sulfanylidene-2H-1,2,4-triazin-5-one
• CAS: 1396681-49-4
• 化学式: C₁₆H₁₁N₅O₄S
• 分子量: 369.36
• InChiKey: BHGISCXGRXLPCJ-QFKQOMIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(2-氯乙基)吗啉 、 6-[(E)-2-(furan-2-yl)ethenyl]-4-[(E)(4-nitrobenzylidene)amino]-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以52%的产率得到6-[(E)-2-(furan-2-yl)ethenyl]-3-[(2-(morpholin-1-yl)ethyl)sulfanyl]-4-[(E)-(4-nitrobenzylidene)amino]-1,2,4-triazin-5(4H)-one
  参考文献：
  名称：

  Synthesis of some (E)-6-[2-(furan-2-yl)ethenyl]-1,2,4-triazin-5-ones and their biological evaluation as antitumor agents

  摘要：

  The synthesis of some new (E)-6-[2-(furan-2-yl)ethenyl]-1,2,4-triazin-5-ones directly linked to either pyrazole, pyrazoline, pyrazolidine counterparts, or to substituted thio and hydrazono functionalities is described. Six of the newly synthesized compounds were selected by the National Cancer Institute (NCI) to be evaluated for their in vitro antitumor activity according to the protocol of the NCI in vitro disease-oriented human cells screening panel assay. The results revealed that the pyrazole derivative 5c was found to be the most active member in this screen as evidenced by its ability to exert potential growth inhibitory activity against most of the tested subpanel tumor cell lines with selective influence on leukemia subpanel tumor cell lines (GI(50) values 2.01-3.03 mu M). Moreover, a comparative study for log GI(50) values of both compound 5c and 5-fluorouracil (5-FU) revealed that compound 5c showed higher potency than 5-FU against most of the tested subpanel tumor cell lines. Thus compound 5c could be considered as a suitable lead towards the design of broad spectrum antitumor active agents targeting various human tumor cell lines.

  DOI：

  10.1007/s00044-012-0192-x
• 作为产物：
  描述：

  (3E)-4-(furan-2-yl)-2-oxobut-3-enoic acid 在 sodium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 1.58h， 生成 6-[(E)-2-(furan-2-yl)ethenyl]-4-[(E)(4-nitrobenzylidene)amino]-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one
  参考文献：
  名称：

  Synthesis of some (E)-6-[2-(furan-2-yl)ethenyl]-1,2,4-triazin-5-ones and their biological evaluation as antitumor agents

  摘要：

  The synthesis of some new (E)-6-[2-(furan-2-yl)ethenyl]-1,2,4-triazin-5-ones directly linked to either pyrazole, pyrazoline, pyrazolidine counterparts, or to substituted thio and hydrazono functionalities is described. Six of the newly synthesized compounds were selected by the National Cancer Institute (NCI) to be evaluated for their in vitro antitumor activity according to the protocol of the NCI in vitro disease-oriented human cells screening panel assay. The results revealed that the pyrazole derivative 5c was found to be the most active member in this screen as evidenced by its ability to exert potential growth inhibitory activity against most of the tested subpanel tumor cell lines with selective influence on leukemia subpanel tumor cell lines (GI(50) values 2.01-3.03 mu M). Moreover, a comparative study for log GI(50) values of both compound 5c and 5-fluorouracil (5-FU) revealed that compound 5c showed higher potency than 5-FU against most of the tested subpanel tumor cell lines. Thus compound 5c could be considered as a suitable lead towards the design of broad spectrum antitumor active agents targeting various human tumor cell lines.

  DOI：

  10.1007/s00044-012-0192-x