benzyl 2(S)-2-benzyloxycarbonylamino-4-oxo-4-[5'-aminosulfamoyl-5'-deoxyadenosine]-butyrate | 548483-95-0

• 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 2(S)-2-benzyloxycarbonylamino-4-oxo-4-[5'-aminosulfamoyl-5'-deoxyadenosine]-butyrate
• CAS: 548483-95-0
• 化学式: C₂₉H₃₁N₇O₁₁S
• 分子量: 685.671
• InChiKey: JXSNUTHKOXAIPI-OZSYYQROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  256.41
• 氢给体数：
  5.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  benzyl 2(S)-2-benzyloxycarbonylamino-4-oxo-4-[5'-aminosulfamoyl-5'-deoxyadenosine]-butyrate 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85%的产率得到(S)-2-Amino-4-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxysulfonylamino]-4-oxo-butyric acid
  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：

  N-苄氧羰基-L-天冬氨酸 1-苄酯 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 benzyl 2(S)-2-benzyloxycarbonylamino-4-oxo-4-[5'-aminosulfamoyl-5'-deoxyadenosine]-butyrate
  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