1-(5'-O-sulfamoyl-2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carbonitrile | 123124-34-5

• 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: 1-(5'-O-sulfamoyl-2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carbonitrile
• 英文别名: 1-(5'-O-sulfamoyl-2',3'-di-O-isopropylidene-β-D-ribofuranosyl)[1,2,4]triazole-3-carbonitrile；[(3aR,4R,6R,6aR)-4-(3-cyano-1,2,4-triazol-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl sulfamate
• CAS: 123124-34-5
• 化学式: C₁₁H₁₅N₅O₆S
• 分子量: 345.336
• InChiKey: JZVFHTQCJIXOFL-PEBGCTIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.21
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  151.58
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-(5'-O-sulfamoyl-2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carbonitrile 在 溶剂黄146 作用下， 反应 2.0h， 以95%的产率得到[(2R,3S,4R,5R)-5-(3-氰基-1,2,4-三唑-1-基)-3,4-二羟基四氢呋喃-2-基]甲基氨基磺酸
  参考文献：
  名称：

  Synthesis, structure, and antiparasitic activity of sulfamoyl derivatives of ribavirin

  摘要：

  The triazole nucleoside derivatives 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-carboxamide (2), 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-thiocarboxamide (3), and 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl)-[1,2,4]triazole-3- carbonitrile (4) were synthesized. Suitably protected triazole nucleosides were converted to their corresponding 5'-sulfamoyl derivatives, which on subsequent deprotection gave the desired compounds in good yields. The structures of compounds 2-4 were confirmed by X-ray crystallographic analysis. All three compounds showed significant antiparasitic activity in vitro, while 2 showed significant activity in vivo against Leishmania donovani and Trypanosoma brucei.

  DOI：

  10.1021/jm00163a008
• 作为产物：
  描述：

  3-氰基-1-(2,3,5-三-O-乙酰基-beta-D-呋喃核糖基)-1,2,4-三唑 在 盐酸 、 高氯酸 、 sodium hydride 作用下， 以 丙酮 为溶剂， 反应 31.67h， 生成 1-(5'-O-sulfamoyl-2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carbonitrile
  参考文献：
  名称：

  Synthesis, structure, and antiparasitic activity of sulfamoyl derivatives of ribavirin

  摘要：

  The triazole nucleoside derivatives 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-carboxamide (2), 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl) [1,2,4]triazole-3-thiocarboxamide (3), and 1-(5'-O-sulfamoyl-beta-D-ribofuranosyl)-[1,2,4]triazole-3- carbonitrile (4) were synthesized. Suitably protected triazole nucleosides were converted to their corresponding 5'-sulfamoyl derivatives, which on subsequent deprotection gave the desired compounds in good yields. The structures of compounds 2-4 were confirmed by X-ray crystallographic analysis. All three compounds showed significant antiparasitic activity in vitro, while 2 showed significant activity in vivo against Leishmania donovani and Trypanosoma brucei.

  DOI：

  10.1021/jm00163a008

文献信息

• KINI, GANESH D.;HENRY, ELIZABETH M.;ROBINS, ROLAND K.;LARSON, STEVEN B.;M+, J. MED. CHEM., 33,(1990) N, C. 44-48
  作者：KINI, GANESH D.、HENRY, ELIZABETH M.、ROBINS, ROLAND K.、LARSON, STEVEN B.、M+

  DOI：——

  日期：——