5-formyl-1-[(2'-deoxy-3',5'-di-O-p-toluoyl)-β-D-erythropentofuranosyl]imidazole-4-carboxamide | 917248-04-5

• 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: 5-formyl-1-[(2'-deoxy-3',5'-di-O-p-toluoyl)-β-D-erythropentofuranosyl]imidazole-4-carboxamide
• CAS: 917248-04-5
• 化学式: C₂₆H₂₅N₃O₇
• 分子量: 491.5
• InChiKey: KOLASMCHBAGQLG-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  139.81
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 5-formyl-1-[(2'-deoxy-3',5'-di-O-p-toluoyl)-β-D-erythropentofuranosyl]imidazole-4-carboxamide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 5-(4,6-diamino-2,5-dihydro-1,3,5-triazin-2-yl)-1-(2'-deoxy-β-D-erythropentofuranosyl)imidazole-4-carboxamide
  参考文献：
  名称：

  A Novel Imidazole Nucleoside Containing a Diaminodihydro-S-triazine as a Substituent: Inhibitory Activity Against the West Nile Virus NTPase/Helicase

  摘要：

  The attempted synthesis of a ring-expanded guanosine (1) containing the imidazo[4,5-e][1,3]diazepine ring system by condensation of 1-(2'-deoxy-beta-D-erythropentofuranosyl)-4-ethoxycarbonylimidazole-5-carbaldehyde (2) with guanidine resulted in the formation of an unexpected product, 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-(2,4-diamino-3,6-dihydro-1,3,5-triazin-6-yl)imidazole-4-carboxamide (7). The structure as well as the pathway of formation of 7 was corroborated by isolation of the intermediate, followed by its conversion to the product. Nucleoside 7 showed promising in vitro anti-helicase activity against the West Nile virus NTPase/ helicase with an IC 50 of 3-10 mu g/mL.

  DOI：

  10.1080/15257770500267063
• 作为产物：
  描述：

  ethyl 5-diethoxymethyl-1-[(2'-deoxy-3',5'-di-O-p-toluoyl)-β-D-erythropentofuranosyl]imidazole-4-carboxylate 在 吡啶 、 氨 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 生成 5-formyl-1-[(2'-deoxy-3',5'-di-O-p-toluoyl)-β-D-erythropentofuranosyl]imidazole-4-carboxamide
  参考文献：
  名称：

  A Novel Imidazole Nucleoside Containing a Diaminodihydro-S-triazine as a Substituent: Inhibitory Activity Against the West Nile Virus NTPase/Helicase

  摘要：

  The attempted synthesis of a ring-expanded guanosine (1) containing the imidazo[4,5-e][1,3]diazepine ring system by condensation of 1-(2'-deoxy-beta-D-erythropentofuranosyl)-4-ethoxycarbonylimidazole-5-carbaldehyde (2) with guanidine resulted in the formation of an unexpected product, 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-(2,4-diamino-3,6-dihydro-1,3,5-triazin-6-yl)imidazole-4-carboxamide (7). The structure as well as the pathway of formation of 7 was corroborated by isolation of the intermediate, followed by its conversion to the product. Nucleoside 7 showed promising in vitro anti-helicase activity against the West Nile virus NTPase/ helicase with an IC 50 of 3-10 mu g/mL.

  DOI：

  10.1080/15257770500267063