5-(p-chlorophenyl)-4-(1,2-O-isopropylidene-α-D-glucofuranos-6-yl)-1,2,4-triazoline-3-thione | 1071856-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(p-chlorophenyl)-4-(1,2-O-isopropylidene-α-D-glucofuranos-6-yl)-1,2,4-triazoline-3-thione
• 英文别名: 4-[(2R)-2-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]-3-(4-chlorophenyl)-1H-1,2,4-triazole-5-thione
• CAS: 1071856-76-2
• 化学式: C₁₇H₂₀ClN₃O₅S
• 分子量: 413.882
• InChiKey: SPJFSZUOPSXFAL-WPLOAARJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,5-di-O-acetyl-6-deoxy-1,2-isopropylidene-6-[(p-chlorobenzohydrazinecarbothionyl)amino]-α-D-glucofuranose 以 sodium hydroxide 为溶剂， 反应 2.0h， 以41%的产率得到5-(p-chlorophenyl)-4-(1,2-O-isopropylidene-α-D-glucofuranos-6-yl)-1,2,4-triazoline-3-thione
  参考文献：
  名称：

  Synthesis and antiviral activity of azoles obtained from carbohydrates

  摘要：

  Herein we describe the synthesis of 1,2,4-triazolyl-3-thione; 1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-alpha-D-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.028

文献信息

• Synthesis and antiviral activity of azoles obtained from carbohydrates
  作者：José Sebastián Barradas、María Inés Errea、Norma B. D’Accorso、Claudia S. Sepúlveda、Laura B. Talarico、Elsa B. Damonte

  DOI：10.1016/j.carres.2008.06.028

  日期：2008.9

  Herein we describe the synthesis of 1,2,4-triazolyl-3-thione; 1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-alpha-D-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. (C) 2008 Elsevier Ltd. All rights reserved.