3-(β-D-galactopyranosyl-(1→4)-(β-D-glucopyranosyl-5-(2-(methylthio)phenyl)))-4H-1,2,4-triazole-4-amine | 1443439-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(β-D-galactopyranosyl-(1→4)-(β-D-glucopyranosyl-5-(2-(methylthio)phenyl)))-4H-1,2,4-triazole-4-amine
• 英文别名: (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-6-[[4-amino-5-(2-methylsulfanylphenyl)-1,2,4-triazol-3-yl]sulfanyl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1443439-19-7
• 化学式: C₂₁H₃₀N₄O₁₀S₂
• 分子量: 562.622
• InChiKey: UOGDYHPAXYLDGX-WAIJYGBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  277
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2-(甲基硫代)苯甲酸 在 吡啶 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.0h， 生成 3-(β-D-galactopyranosyl-(1→4)-(β-D-glucopyranosyl-5-(2-(methylthio)phenyl)))-4H-1,2,4-triazole-4-amine
  参考文献：
  名称：

  Synthesis, Antiviral, and Antimicrobial Activity of 1,2,4-Triazole Thioglycoside Derivatives

  摘要：

  The reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with glucosyl, galactosyl, lactosyl bromide, and peracetylated ribose under the conventional and microwave irradiation methods afforded the corresponding S-glycosides. Deacetylation of S-glycosides gave the corresponding deacetylated derivatives. Reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with 4-acetoxybutyl bromide, 2-acetoxyethoxymethyl bromide, 3-chloropropanol, 1,3-dichloroopropan-2-ol, epichlorohydrin, allyl bromide, and propargayl bromide gave the corresponding S-acyclonucleosides, which were deacetylated to give the corresponding deacetylated compounds. All the newly synthesized compounds were characterized by the IR, H-1, C-13 NMR, and elemental analyses. Some of these compounds were screened for their antiviral and antimicrobial activity.

  DOI：

  10.1080/10426507.2012.668990

文献信息

• Synthesis, Antiviral, and Antimicrobial Activity of 1,2,4-Triazole Thioglycoside Derivatives
  作者：Hassan A. El-Sayed、Ahmed H. Moustafa、Abd El-Fattah Z. Haikal

  DOI：10.1080/10426507.2012.668990

  日期：2013.5.1

  The reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with glucosyl, galactosyl, lactosyl bromide, and peracetylated ribose under the conventional and microwave irradiation methods afforded the corresponding S-glycosides. Deacetylation of S-glycosides gave the corresponding deacetylated derivatives. Reaction of 5-(2-methylthio)phenyl-1,2,4-triazole-3-thiol with 4-acetoxybutyl bromide, 2-acetoxyethoxymethyl bromide, 3-chloropropanol, 1,3-dichloroopropan-2-ol, epichlorohydrin, allyl bromide, and propargayl bromide gave the corresponding S-acyclonucleosides, which were deacetylated to give the corresponding deacetylated compounds. All the newly synthesized compounds were characterized by the IR, H-1, C-13 NMR, and elemental analyses. Some of these compounds were screened for their antiviral and antimicrobial activity.