7-deaza-6-(p-methoxycarbonylbenzylthio)inosine | 1039752-98-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 7-deaza-6-(p-methoxycarbonylbenzylthio)inosine
• 英文别名: 4-[(4-methoxycarbonylbenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine；4-[(4-Methoxycarbonylbenzyl)thio]-7-(beta-D-ribofuranosyl)-7Hpyrrolo[2,3-d]pyrimidine；methyl 4-[[7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidin-4-yl]sulfanylmethyl]benzoate
• CAS: 1039752-98-1
• 化学式: C₂₀H₂₁N₃O₆S
• 分子量: 431.469
• InChiKey: YQBGKBNMFIMFAY-YKTARERQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-chloro-7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidine 、 methyl 4-(mercaptomethyl)benzoate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到7-deaza-6-(p-methoxycarbonylbenzylthio)inosine
  参考文献：
  名称：

  Structure−Activity Relationships of 7-Deaza-6-benzylthioinosine Analogues as Ligands ofToxoplasma gondiiAdenosine Kinase

  摘要：

  Several 7-deaza-6-benzylthioinosine analogues with varied substituents on aromatic ring were synthesized and evaluated against Toxoplasma gondii adenosine kinase (EC.2.7.1.20). Structure-activity relationships indicated that the nitrogen atom at the 7-position does not appear to be a critical structural requirement. Molecular modeling reveals that the 7-deazapurine motif provided flexibility to the 6-benzylthio group as a result of the absence of H-bonding between N7 and Thr140. This flexibility allowed better fitting of the 6-benzylthio group into the hydrophobic pocket of the enzyme at the 6-position. In general, single substitutions at the para or meta position enhanced binding. On the other hand., single substitutions at the ortho position led to the loss of binding affinity. The most potent compounds, 7-deaza-p-cyano-6-benzylthioinosine (IC(50) = 5.3 mu M) and 7-deaza-p-methoxy-6-benzylthioinosine (IC(50) = 4.6 mu M), were evaluated in cell culture to delineate their selective toxicity.

  DOI：

  10.1021/jm800201s