[(2R,3S,4R,5R)-5-(3-硫代氨基甲酰-1,2,4-三唑-1-基)-3,4-二羟基四氢呋喃-2-基]甲基氨基磺酸 | 123124-29-8

• 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: [(2R,3S,4R,5R)-5-(3-硫代氨基甲酰-1,2,4-三唑-1-基)-3,4-二羟基四氢呋喃-2-基]甲基氨基磺酸
• 中文别名: 1-(5'-O-氨磺酰-β-呋喃核糖基)(1,2,4)三唑-3-硫代甲酰胺
• 英文名称: 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)<1,2,4>triazole-3-thiocarboxamide
• 英文别名: 1-(5'-O-sulfamoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-thiocarboxamide；1-(5'-O-Sulfamoyl-beta-ribofuranosyl)(1,2,4)triazole-3-thiocarboxamide；[(2R,3S,4R,5R)-5-(3-carbamothioyl-1,2,4-triazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate
• CAS: 123124-29-8
• 化学式: C₈H₁₃N₅O₆S₂
• 分子量: 339.353
• InChiKey: PGHJZJNBFSOFNB-AFCXAGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 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：
  183
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-(5'-O-sulfamoyl-2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-thiocarboxamide 在 溶剂黄146 作用下， 反应 4.0h， 以62.5%的产率得到[(2R,3S,4R,5R)-5-(3-硫代氨基甲酰-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

文献信息

• 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.
• US4992426A
  申请人：——

  公开号：US4992426A

  公开（公告）日：1991-02-12
• [EN] PRE-ACTIVATED NUCLEOSIDE IMPDH INHIBITORS AS ANTI-INFECTIVE DRUGS<br/>[FR] INHIBITEURS NUCLÉOSIDIQUES D'IMPDH PRÉ-ACTIVÉS EN TANT QUE MÉDICAMENTS ANTI-INFECTIEUX
  申请人：OCTAGON THERAPEUTICS INC

  公开号：WO2020072931A2

  公开（公告）日：2020-04-09

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