1-β-D-ribofuranosyl<1,2,4>triazole-3-carbonitrile | 123147-83-1

• 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-β-D-ribofuranosyl<1,2,4>triazole-3-carbonitrile
• 英文别名: 1-β-D-ribofuranozyl-1,2,4-triazole 3-carbonitrile；1-(β-D-ribofuranosyl)[1,2,4]triazole-3-carbonitrile；1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-[1,2,4]triazole-3-carbonitrile；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carbonitrile
• CAS: 123147-83-1
• 化学式: C₈H₁₀N₄O₄
• 分子量: 226.192
• InChiKey: JCLUSIUTVRQXRU-XVFCMESISA-N

物化性质

• 沸点：
  577.9±60.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-β-D-ribofuranosyl<1,2,4>triazole-3-carbonitrile 在 高氯酸 、 sodium hydride 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 9.67h， 生成 [(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 作用下， 反应 24.0h， 以91%的产率得到1-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

• Chemoenzymatic method of 1,2,4-triazole nucleoside synthesis: Possibilities and limitations
  作者：I. D. Konstantinova、M. V. Chudinov、I. V. Fateev、A. V. Matveev、N. I. Zhurilo、V. I. Shvets、A. I. Miroshnikov

  DOI：10.1134/s1068162013010056

  日期：2013.1

  of novel structural analogues of an antiviral preparation of Ribavirin (1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide) were established. A synthesis of various amides of 1H-1,2,4-triazole-3-carboxylic acid and its 5-substituted analogues—potential substrates of purine nucleoside phosphorylase—has been described. Comparative efficiency of preparation methods of these amides, as well as the methods

  确定了利巴韦林（1-β-D-呋喃核糖基-1,2,4-三唑-3-甲酰胺）抗病毒制剂的新型结构类似物的化学酶促合成的可能性和局限性。已经描述了 1H-1,2,4-三唑-3-羧酸及其 5-取代类似物（嘌呤核苷磷酸化酶的潜在底物）的各种酰胺的合成。研究了这些酰胺的制备方法的比较效率，以及将官能团引入杂环系统的C5位置的方法。合成了在羧酰胺组中含有各种取代基的新型病毒唑类似物。开发了一种生物技术方法来制备 1-β-D-呋喃核糖基-1,2,4-三唑-3-羰基，这是一种合成病毒脒（病毒唑的现代类似物）的中间体。
• ANTIVIRAL PHOSPHONATE ANALOGS
  申请人：Boojamra Constantine G.

  公开号：US20090275535A1

  公开（公告）日：2009-11-05

  The invention is related to phosphorus substituted compounds with antiviral activity, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  这项发明涉及具有抗病毒活性的磷取代化合物，包含这种化合物的组合物以及包括给予这种化合物的治疗方法，还包括用于制备这种化合物的过程和中间体。
• 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：——
• Nucleoside Phosphonate Analogs
  申请人：Boojamra Constantine G.

  公开号：US20110071101A1

  公开（公告）日：2011-03-24

  The invention is related to phosphorus substituted nucleoside compounds and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.
• US3991078A
  申请人：——

  公开号：US3991078A

  公开（公告）日：1976-11-09