5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide | 110882-65-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide
• 英文别名: 5-cyano-1-β-D-ribofuranosylimidazole-4-carboxamide；5-cyano-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]imidazole-4-carboxamide；5-cyano-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
• CAS: 110882-65-0
• 化学式: C₁₀H₁₂N₄O₅
• 分子量: 268.229
• InChiKey: UAMHODYXEGPSMN-VPCXQMTMSA-N

物化性质

• 沸点：
  761.9±60.0 °C(Predicted)
• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide 在 吡啶 、 三氯硫磷 、 1,8-双二甲氨基萘 作用下， 反应 0.5h， 生成 5-ethynyl-1-(5-O-thiophosphono-β-D-ribofuranosyl)imidazole-4-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：

  5-iodo-1-(2,3,5-tri-0-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 在 ozone-containing oxygen 、 二(氰基苯)二氯化钯 、 二甲基硫 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 26.33h， 生成 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide
  参考文献：
  名称：

  Nucleosides and Nucleotides. 140. Synthesis and Antileukemic Activity of 5-Carbon-Substituted 1-β-d-Ribofuflranosylimidazole-4-Carboxamides

  摘要：

  Synthesis of 5-carbon-substituted 1-beta-D-ribofuranosylimidazole-4-carboxamides are described. Treatment of 5-iodo derivative 8 with methyl acrylate in the presence of palladium catalyst gave (E)-5-(2-carbomethoxyvinyl)-1-(2,3,5-tri-O-acetyl- beta-D-ribofuranosyl)imidazole-4-carboxamide (9), followed by appropriate manipulations to afford various 5-carbon-substituted imidazole derivatives 1-7. The antileukemic activities of these imidazole nucleosides are also described.

  DOI：

  10.1080/07328319608002383

文献信息

• Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases
  作者：Guangyi Wang、Kandasamy Sakthivel、Vasanthakumar Rajappan、Thomas W. Bruice、Kathleen Tucker、Patrick Fagan、Jennifer L. Brooks、Tiffany Hurd、Janet M. Leeds、P. Dan Cook

  DOI：10.1081/ncn-120027838

  日期：2004.1.1

  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.
• Nucleosides and Nucleotides. 140. Synthesis and Antileukemic Activity of 5-Carbon-Substituted 1-β-<scp>d</scp>-Ribofuflranosylimidazole-4-Carboxamides
  作者：Noriaki Minakawa、Naoshi Kojima、Takuma Sasaki、Akira Matsuda

  DOI：10.1080/07328319608002383

  日期：1996.1

  Synthesis of 5-carbon-substituted 1-beta-D-ribofuranosylimidazole-4-carboxamides are described. Treatment of 5-iodo derivative 8 with methyl acrylate in the presence of palladium catalyst gave (E)-5-(2-carbomethoxyvinyl)-1-(2,3,5-tri-O-acetyl- beta-D-ribofuranosyl)imidazole-4-carboxamide (9), followed by appropriate manipulations to afford various 5-carbon-substituted imidazole derivatives 1-7. The antileukemic activities of these imidazole nucleosides are also described.