N-2-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(E)-4-(benzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione | 1198308-28-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-2-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(E)-4-(benzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-[(E)-benzylideneamino]-3-phenyl-5-sulfanylidene-1,2,4-triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 1198308-28-9
• 化学式: C₂₉H₃₀N₄O₉S
• 分子量: 610.645
• InChiKey: FRAUEDYWWNBICX-NLSYWKHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (E)-4-(benzylideneamino)-5-phenyl-4H-1,2,4-triazole-3-thiol 、 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61%的产率得到N-2-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(E)-4-(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

文献信息

• Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified d-glucopyranosyl residues and their antiproliferative activities
  作者：Zhizhang Li、Zheng Gu、Kai Yin、Rong Zhang、Qin Deng、Jiannan Xiang

  DOI：10.1016/j.ejmech.2009.05.030

  日期：2009.11

  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.