1-(2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carbonitrile | 69313-77-5

• 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-(2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carbonitrile
• 英文别名: 3-cyano-1-(2,3-O-iso-propylidene-β-D-ribofuranosyl)-1,2,4-triazole；1-(2',3'-di-O-isopropylidene-β-D-ribofuranosyl)[1,2,4]triazole-3-carbonitrile；1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,2,4-triazole-3-carbonitrile
• CAS: 69313-77-5
• 化学式: C₁₁H₁₄N₄O₄
• 分子量: 266.257
• InChiKey: GSIPEJHNQVUBOF-PEBGCTIMSA-N

物化性质

• 沸点：
  475.7±55.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carbonitrile 以50%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：
• 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 作用下， 以 丙酮 为溶剂， 反应 25.5h， 生成 1-(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：——
• US4138547A
  申请人：——

  公开号：US4138547A

  公开（公告）日：1979-02-06
• Synthesis, structure, and antiparasitic activity of sulfamoyl derivatives of ribavirin
  作者：Ganesh D. Kini、Elizabeth M. Henry、Roland K. Robins、Steven B. Larson、J. Joseph Marr、Randolph L. Berens、Cyrus J. Bacchi、Henry C. Nathan、Jan S. Keithly

  DOI：10.1021/jm00163a008

  日期：1990.1

  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.