({[(2R,3S,4R,5R)-5-(3-Carbamoyl-[1,2,4]triazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-amino}-methyl)-phosphonic acid diethyl ester | 594860-52-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: ({[(2R,3S,4R,5R)-5-(3-Carbamoyl-[1,2,4]triazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-amino}-methyl)-phosphonic acid diethyl ester
• CAS: 594860-52-3
• 化学式: C₁₃H₂₄N₅O₇P
• 分子量: 393.337
• InChiKey: YSYWVJMPUCCGCH-VWMGYNLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.19
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  171.05
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ({[(2R,3S,4R,5R)-5-(3-Carbamoyl-[1,2,4]triazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-amino}-methyl)-phosphonic acid diethyl ester 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以13.5 mg的产率得到1-(5-deoxy-5-N-phosphonomethylamino-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide
  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：

  1-(5-deoxy-5-iodo-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、206.84 kPa 条件下， 反应 31.5h， 生成 ({[(2R,3S,4R,5R)-5-(3-Carbamoyl-[1,2,4]triazol-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-amino}-methyl)-phosphonic acid diethyl ester
  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