monolithium mono(((2R,3S,4R,5R)-5-(8-((4-(tert-butyl)benzyl)thio)-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate) | 78711-02-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: monolithium mono(((2R,3S,4R,5R)-5-(8-((4-(tert-butyl)benzyl)thio)-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate)
• CAS: 78711-02-1
• 化学式: C₂₁H₂₅N₄O₈PS*2Li
• 分子量: 538.373
• InChiKey: PJVGBFCUBDUHQA-ZPXBPYQOSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -2.82
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  185.68
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  对叔丁基苄硫醇 、 8-bromoinosine 5'-phosphate dilithium salt 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以13%的产率得到monolithium mono(((2R,3S,4R,5R)-5-(8-((4-(tert-butyl)benzyl)thio)-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate)
  参考文献：
  名称：

  Inhibition of inosinic acid dehydrogenase by 8-substituted purine nucleotides

  摘要：

  A series of 8-substituted derivatives of adenosine monophosphate (AMP) and inosine monophosphate (IMP) were synthesized and examined for their ability to inhibit Escherichia coli IMP dehydrogenase. All compounds studied were competitive inhibitors in IMP-dependent competition studies and lacked substrate activity. In oxidized nicotinamide adenine dinucleotide dependent studies, 8-(p-NO2PhCH2S)-IMP was noncompetitive and 8-(p-NO2PhCH2S)-AMP showed mixed inhibition. Multiple regression analysis showed that for the series of 8-(para-substituted-benzylthio)-AMPs and -IMPs, the electron-withdrawing ability of the para substituent on the benzylthio moiety correlated best with log Ki of the analogues.

  DOI：

  10.1021/jm00142a007