5-N-phenylaminomethyl-2-(β-D-glucopyranosyl)sulfanyl-1,3,4-oxadiazole | 1064194-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-N-phenylaminomethyl-2-(β-D-glucopyranosyl)sulfanyl-1,3,4-oxadiazole
• 英文别名: (2S,3R,4S,5S,6R)-2-[[5-(anilinomethyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1064194-54-2
• 化学式: C₁₅H₁₉N₃O₆S
• 分子量: 369.398
• InChiKey: NLYAHKKYXIIAGV-LPUQOGTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-N-phenylaminomethyl-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)sulfanyl-1,3,4-oxadiazole 在 甲醇 、 氨 作用下， 反应 5.5h， 以70%的产率得到5-N-phenylaminomethyl-2-(β-D-glucopyranosyl)sulfanyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of Some 5‐N‐Arylaminomethyl‐2‐glycosylsulphanyl‐1,3,4‐oxadiazoles and Their Analogs against Hepatitis A and Herpes Simplex Viruses

  摘要：

  N-Arylaminomethyl-3H-1,3,4-oxadiazole-2-thiones 2a,b were prepared from the corresponding N-arylglycinoylhydrazides. A number of their thioglycoside derivatives 4-7a-c and S-functionalized analogs 8-11a,b were synthesized by the reaction with different acetobromosugars and acyclic hydroxyalkylating agents. The antiviral activity of a number of the synthesized compounds against herpes simplex virus type 1 (HSV-1) and hepatitis A virus (HAV) was evaluated. Compounds 5a and 5b showed promising results against HAV.

  DOI：

  10.1080/07328300802262778

文献信息

• Synthesis and Antiviral Evaluation of Some 5‐<i>N</i>‐Arylaminomethyl‐2‐glycosylsulphanyl‐1,3,4‐oxadiazoles and Their Analogs against Hepatitis A and Herpes Simplex Viruses
  作者：Wael A. El‐Sayed、Nahed M. Fathi、W. A. Gad、El Sayed H. El‐Ashry

  DOI：10.1080/07328300802262778

  日期：2008.8

  N-Arylaminomethyl-3H-1,3,4-oxadiazole-2-thiones 2a,b were prepared from the corresponding N-arylglycinoylhydrazides. A number of their thioglycoside derivatives 4-7a-c and S-functionalized analogs 8-11a,b were synthesized by the reaction with different acetobromosugars and acyclic hydroxyalkylating agents. The antiviral activity of a number of the synthesized compounds against herpes simplex virus type 1 (HSV-1) and hepatitis A virus (HAV) was evaluated. Compounds 5a and 5b showed promising results against HAV.