benzyl 3-oxo-3-[5'-aminosulfamoyl-5'-deoxyadenosine]-propylcarbamate | 548483-94-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: benzyl 3-oxo-3-[5'-aminosulfamoyl-5'-deoxyadenosine]-propylcarbamate
• CAS: 548483-94-9
• 化学式: C₂₁H₂₅N₇O₉S
• 分子量: 551.537
• InChiKey: YYTJUHBUZRQUFX-AEVYOOLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.28
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  230.11
• 氢给体数：
  5.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-oxo-3-[5'-aminosulfamoyl-5'-deoxyadenosine]-propylcarbamate 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 以87%的产率得到[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(3-aminopropanoyl)sulfamate
  参考文献：
  名称：

  Synthesis and Characterization of an N-Acylsulfonamide Inhibitor of Human Asparagine Synthetase

  摘要：

  The synthesis of N-acylsulfonamide 6, which is an analogue of beta-aspartyl-AMP, is described. This compound appears to be the first and only potent inhibitor of human asparagine synthetase that has been described to date. The N-acylsulfonamide 6 exhibits slow-onset inhibition kinetics, with a K-1* of 728 nM. Preparation and characterization of two additional N-acylsulfonamide analogues has also demonstrated the importance of hydrogen-bonding interactions in the recognition of the AS inhibitor with the enzyme. These observations provide the basis for the discovery of new compounds with application in the treatment of drug-resistant leukemia.

  DOI：

  10.1021/ol034212n
• 作为产物：
  描述：

  benzyl 3-oxo-3-[5'-aminosulfamoyl-5'-deoxy-2',3'-O-isopropylidene-adenosine]-propylcarbamate 在 三氟乙酸 作用下， 反应 3.0h， 以80%的产率得到benzyl 3-oxo-3-[5'-aminosulfamoyl-5'-deoxyadenosine]-propylcarbamate
  参考文献：
  名称：

  Synthesis and Characterization of an N-Acylsulfonamide Inhibitor of Human Asparagine Synthetase

  摘要：

  The synthesis of N-acylsulfonamide 6, which is an analogue of beta-aspartyl-AMP, is described. This compound appears to be the first and only potent inhibitor of human asparagine synthetase that has been described to date. The N-acylsulfonamide 6 exhibits slow-onset inhibition kinetics, with a K-1* of 728 nM. Preparation and characterization of two additional N-acylsulfonamide analogues has also demonstrated the importance of hydrogen-bonding interactions in the recognition of the AS inhibitor with the enzyme. These observations provide the basis for the discovery of new compounds with application in the treatment of drug-resistant leukemia.

  DOI：

  10.1021/ol034212n