3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-5-(2-(methylthio)phenyl)-4H-1,2,4-triazole-4-amine | 1443439-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-5-(2-(methylthio)phenyl)-4H-1,2,4-triazole-4-amine
• 英文别名: [(2R,3R,4R,5S)-3,4-diacetyloxy-5-[[4-amino-5-(2-methylsulfanylphenyl)-1,2,4-triazol-3-yl]sulfanyl]oxolan-2-yl]methyl acetate
• CAS: 1443439-16-4
• 化学式: C₂₀H₂₄N₄O₇S₂
• 分子量: 496.565
• InChiKey: XICOCZOAACGPDU-MYZZLAAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  196
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-5-(2-(methylthio)phenyl)-4H-1,2,4-triazole-4-amine 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以88%的产率得到3-(β-D-ribofuranosylmercapto)-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
• 作为产物：
  描述：

  2-(甲基硫代)苯甲酸 在 吡啶 、 silica gel 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.08h， 生成 3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosylmercapto)-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