(E)-4-(4-hydroxy-3-methoxybenzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione | 1198308-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-4-(4-hydroxy-3-methoxybenzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione
• 英文别名: 4-{[(E)-3-Mercapto-5-phenyl-[1,2,4]triazol-4-ylimino]-methyl}-2-methoxy-phenol；4-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-3-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 1198308-26-7
• 化学式: C₁₆H₁₄N₄O₂S
• 分子量: 326.379
• InChiKey: ULUUPBXLBTXAFU-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-hydroxy-3-methoxybenzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione 、 乙酰溴葡糖 在 4-二甲氨基吡啶 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以63%的产率得到N-2-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(E)-4-(4-hydroxy-3-methoxy benzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione
  参考文献：
  名称：

  Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified d-glucopyranosyl residues and their antiproliferative activities

  摘要：

  A series of D-glucopyranosyl-1,2,4-triazole-3-thione derivatives 1a-1d were synthesized by the reaction of 1,2,4-triazole-3-thione Schiff bases 5a-5d with 2,3,4,6-tetra-O-acetyl-sigma-D-glucopyranosyl bromide. We demonstrate the conversion of 2 to 5, without the necessity of purification of both oxadiazole and triazole intermediates to afford the compounds 5. Their structures were confirmed by standard studies of H-1 NMR, IR, MS and elemental analysis. Analogues 5 and 1 have shown cytotoxic activity against human MCF-7 and Bel-7402 malignant cell lines. Crown Copyright (C) 2009 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.030
• 作为产物：
  描述：

  香草醛 、 4-氨基-5-苯基-4H-1,2,4-三唑-3-硫醇 在 溶剂黄146 作用下， 反应 0.17h， 以80%的产率得到(E)-4-(4-hydroxy-3-methoxybenzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione
  参考文献：
  名称：

  Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified d-glucopyranosyl residues and their antiproliferative activities

  摘要：

  A series of D-glucopyranosyl-1,2,4-triazole-3-thione derivatives 1a-1d were synthesized by the reaction of 1,2,4-triazole-3-thione Schiff bases 5a-5d with 2,3,4,6-tetra-O-acetyl-sigma-D-glucopyranosyl bromide. We demonstrate the conversion of 2 to 5, without the necessity of purification of both oxadiazole and triazole intermediates to afford the compounds 5. Their structures were confirmed by standard studies of H-1 NMR, IR, MS and elemental analysis. Analogues 5 and 1 have shown cytotoxic activity against human MCF-7 and Bel-7402 malignant cell lines. Crown Copyright (C) 2009 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.030