三氮唑核苷5'-氨基磺酸 | 120615-22-7

• 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
• 中文名称: 三氮唑核苷5'-氨基磺酸
• 英文名称: 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)<1,2,4>triazole-3-carboxamide
• 英文别名: 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide；1-(5'-O-sulfamoyl-β-D-ribofuranosyl)[1,2,4]triazole-3-carboxamide；Ribavirin 5'-sulfamate；[(2R,3S,4R,5R)-5-(3-carbamoyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate
• CAS: 120615-22-7
• 化学式: C₈H₁₃N₅O₇S
• 分子量: 323.287
• InChiKey: XNONLXYJUOPNLN-AFCXAGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  利巴韦林 在 高氯酸 、 sodium hydride 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 9.75h， 生成 三氮唑核苷5'-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

文献信息

• Modulation of TH1/TH2 cytokine expression by ribavirin and ribavirin analogs in activated t-lymphocytes
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP1174141A2

  公开（公告）日：2002-01-23

  Ribavirin is administered to a patient in a dosage range which is effective to modulate lymphokine expression in activated T cells. In particular, Ribavirin is used to suppress Th2-mediated T cell responses and promote Th1 -mediated T cell responses. In other aspects of the invention, one or more Ribavirin analogs are administered to a patient in a dosage range which is effective to modulate lymphokine expression in activated T cells. The Ribavirin analog(s) may be used to suppress or enhance Th1 or Th2-mediated T cell responses.

  给病人服用利巴韦林的剂量范围能有效调节活化 T 细胞中淋巴因子的表达。特别是，利巴韦林可用于抑制Th2介导的T细胞反应，促进Th1介导的T细胞反应。在本发明的其他方面，向患者施用一种或多种利巴韦林类似物，其剂量范围可有效调节活化 T 细胞中淋巴因子的表达。利巴韦林类似物可用于抑制或增强 Th1 或 Th2 介导的 T 细胞反应。
• Modulation of Th1/Th2 Cytokine expression by Ribavirin and Ribavirin analogs in actived T-Lymphocytes for treating HCV infections
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP1240899A2

  公开（公告）日：2002-09-18

  Ribavirin® is administered to a patient in a dosage range which is effective to modulate lymphokine expression in activated T cells. In particular, Ribavirin® is used to suppress Th2-mediated T cell responses and promote Th1-mediated T cell response. In other apsects of the invention, one or more Ribavirin® analogs are administered to a patient in a dosage range which is effective to modulate lymphokine expression in activated T cells. The Ribavirin® analog(s) may be used to suppress or enhance Th1 or Th2-mediated T cell responses.

  利巴韦林®给患者的剂量范围可有效调节活化 T 细胞中淋巴因子的表达。特别是，利巴韦林®可用于抑制Th2介导的T细胞反应，促进Th1介导的T细胞反应。在本发明的其他部分中，向患者施用一种或多种利巴韦林® 类似物，其剂量范围可有效调节活化 T 细胞中淋巴因子的表达。利巴韦林® 类似物可用于抑制或增强 Th1 或 Th2 介导的 T 细胞反应。
• MODULATION OF TH1/TH2 CYTOKINE EXPRESSION BY RIBAVIRIN$m(3) AND RIBAVIRIN$m(3) ANALOGS IN ACTIVATED T-LYMPHOCYTES
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP0879056A1

  公开（公告）日：1998-11-25
• EP0879056A4
  申请人：——

  公开号：EP0879056A4

  公开（公告）日：1999-01-13
• Pre-Activated Nucleoside IMPDH Inhibitors As Anti-Infective Drugs
  申请人：Octagon Therapeutics Inc.

  公开号：US20210353660A1

  公开（公告）日：2021-11-18

  The present disclosure provides inosine-5′-monophosphate dehydrogenase (IMPDH)-inhibiting nucleoside derivatives having anti-infective activities, and methods of their synthesis and use.