4-carbamoyl-1-[2-O-acetyl-3-O-benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-β-D-ribofuranosyl]-1,3-imidazolium-5-olate | 594860-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-carbamoyl-1-[2-O-acetyl-3-O-benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-β-D-ribofuranosyl]-1,3-imidazolium-5-olate
• 英文别名: [(2R,3R,4R,5R)-2-(4-carbamoyl-5-hydroxyimidazol-1-yl)-5-(2-diethoxyphosphoryl-2,2-difluoroethyl)-4-phenylmethoxyoxolan-3-yl] acetate
• CAS: 594860-66-9
• 化学式: C₂₃H₃₀F₂N₃O₉P
• 分子量: 561.476
• InChiKey: RTYHRPYRVQWMHF-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  161.43
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-carbamoyl-1-[2-O-acetyl-3-O-benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-β-D-ribofuranosyl]-1,3-imidazolium-5-olate 在 三甲基溴硅烷 、 三氯化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.0h， 生成 4-carbamoyl-1-[5,6-dideoxy-6-(dihydroxyphosphinyl)-6,6-difluoro-β-D-ribofuranosyl]-1,3-imidazolium-5-olate
  参考文献：
  名称：

  Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases

  摘要：

  IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5'-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not assured, and usually is inefficient. In order to bypass cellular phosphorylation, a series of azole nucleoside 5'-MP mimics (P1Ms) based on ribavirin, EICAR and bredinin were synthesized and screened against human and C. albicans IMP dehydrogenises. P1Ms 8, 16, 25, 28 and 29 demonstrated substantial IMPDH inhibition with K-i values in low micromolar range.

  DOI：

  10.1081/ncn-120027838
• 作为产物：
  描述：

  [(3R,4R,5R)-2-acetyloxy-5-(2-diethoxyphosphoryl-2,2-difluoroethyl)-4-phenylmethoxyoxolan-3-yl] acetate 、 5-羟基-1H-咪唑-4-甲酰胺 在 ammonium sulfate 、 六甲基二硅氮烷 、 四氯化钛 作用下， 以 xylene 、 硝基甲烷 为溶剂， 反应 42.0h， 以280 mg的产率得到4-carbamoyl-1-[2-O-acetyl-3-O-benzyl-5,6-dideoxy-6-(diethoxyphosphinyl)-6,6-difluoro-β-D-ribofuranosyl]-1,3-imidazolium-5-olate
  参考文献：
  名称：

  Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases

  摘要：

  IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5'-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not assured, and usually is inefficient. In order to bypass cellular phosphorylation, a series of azole nucleoside 5'-MP mimics (P1Ms) based on ribavirin, EICAR and bredinin were synthesized and screened against human and C. albicans IMP dehydrogenises. P1Ms 8, 16, 25, 28 and 29 demonstrated substantial IMPDH inhibition with K-i values in low micromolar range.

  DOI：

  10.1081/ncn-120027838