4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(β-D-ribofuranosyl)imidazole-5-carbonitrile | 160593-87-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(β-D-ribofuranosyl)imidazole-5-carbonitrile
• 英文别名: 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)imidazole-4-carbonitrile
• CAS: 160593-87-3
• 化学式: C₁₂H₁₃N₅O₅
• 分子量: 307.266
• InChiKey: ZMODHSJYNHSFTD-UGKPPGOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(β-D-ribofuranosyl)imidazole-5-carbonitrile 在 ammonium hydroxide 、 双氧水 作用下， 反应 1.5h， 以79%的产率得到4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(β-D-ribofuranosyl)imidazole-5-carboxamide
  参考文献：
  名称：

  Synthesis and Biological Activity of 4-Amino-1-(β-D-ribofuranosyl)imidazo[4,5-d]pyridazin-7-one

  摘要：

  The Lewis acid catalyzed ribosylation of 5(4)-cyano-4(5)-(5-methyl-1,2,4-oxadiazol-3-yl)-1H-imidazole (2) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribose gave only 4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazole-5-carbonitrile (3). Treatment of 3 with methanolic ammonia gave 4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(beta-D-ribofuranosyl)imidazole-5-carbonitrile (4). Treatment of 4 with hydrogen peroxide in ammonia gave 4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(beta-D-ribofuranosyl)imidazole-5-carboxamide (5). When 5 was treated with sodium hydride in dimethyl-sulfoxide a rearrangement (mononuclear heterocyclic rearrangement, m.h.r.) occurred to give a modest 17% yield of 4-acetamido-1-(beta-D ribofuranosyl)imidazo[4,5-d]pyridazin-7-one (6). Treatment of 6 with aqueous ammonia gave 4-amino-1-(beta-D-ribofuranosyl)imidazo [4,5-d]pyridazin-7-one(1). The synthesis of compound 1 using the m.h.r. for the preparation of a single regioisomer of the imidazo[4,5-d]pyridazin-7-one ring system, has demonstrated the potential of this methodology. Neither compound 5 nor 6 affected the growth or replication of human foreskin fibroblasts (HFF cells) or human cytomegalovirus (HCMV). In contrast, compound 1 inhibited the replication of HCMV (IC50=29 mu M) but produced visual cytotoxicity in uninfected HFF cells (IC50=70 mu M). Compound 1 also inhibited the proliferation of L1210 murine leukemic cells (IC50=25 mu M), whereas the precursors 4 and 6 did not.

  DOI：

  10.1080/15257779408010678
• 作为产物：
  描述：

  4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-5-carbonitrile 在 氨 作用下， 以 甲醇 为溶剂， 以81%的产率得到4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(β-D-ribofuranosyl)imidazole-5-carbonitrile
  参考文献：
  名称：

  Synthesis and Biological Activity of 4-Amino-1-(β-D-ribofuranosyl)imidazo[4,5-d]pyridazin-7-one

  摘要：

  The Lewis acid catalyzed ribosylation of 5(4)-cyano-4(5)-(5-methyl-1,2,4-oxadiazol-3-yl)-1H-imidazole (2) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribose gave only 4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazole-5-carbonitrile (3). Treatment of 3 with methanolic ammonia gave 4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(beta-D-ribofuranosyl)imidazole-5-carbonitrile (4). Treatment of 4 with hydrogen peroxide in ammonia gave 4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(beta-D-ribofuranosyl)imidazole-5-carboxamide (5). When 5 was treated with sodium hydride in dimethyl-sulfoxide a rearrangement (mononuclear heterocyclic rearrangement, m.h.r.) occurred to give a modest 17% yield of 4-acetamido-1-(beta-D ribofuranosyl)imidazo[4,5-d]pyridazin-7-one (6). Treatment of 6 with aqueous ammonia gave 4-amino-1-(beta-D-ribofuranosyl)imidazo [4,5-d]pyridazin-7-one(1). The synthesis of compound 1 using the m.h.r. for the preparation of a single regioisomer of the imidazo[4,5-d]pyridazin-7-one ring system, has demonstrated the potential of this methodology. Neither compound 5 nor 6 affected the growth or replication of human foreskin fibroblasts (HFF cells) or human cytomegalovirus (HCMV). In contrast, compound 1 inhibited the replication of HCMV (IC50=29 mu M) but produced visual cytotoxicity in uninfected HFF cells (IC50=70 mu M). Compound 1 also inhibited the proliferation of L1210 murine leukemic cells (IC50=25 mu M), whereas the precursors 4 and 6 did not.

  DOI：

  10.1080/15257779408010678