1-β-D-ribofuranosyl<1,2,4>triazole-3-thiocarboxamide | 40371-98-0

• 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-thiocarboxamide
• 英文别名: 1-(β-D-Ribofuranosyl)-<1,2,4>triazol-3-thiocarboxamid；1-β-D-ribofuranosyl-1H-[1,2,4]triazole-3-carbothioic acid amide；1-(β-D-ribofuranosyl)-1,2,4-triazole-3-thiocarboxamide；1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-[1,2,4]triazole-3-carbothioic acid amide；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carbothioamide
• CAS: 40371-98-0
• 化学式: C₈H₁₂N₄O₄S
• 分子量: 260.274
• InChiKey: UQSPFUMMCXCDLF-AFCXAGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  126
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-β-D-ribofuranosyl<1,2,4>triazole-3-thiocarboxamide 在 高氯酸 、 sodium hydride 作用下， 以 丙酮 为溶剂， 反应 4.75h， 生成 1-(5'-O-sulfamoyl-2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-thiocarboxamide
  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 、 三乙胺 、 硫化氢 、 硫代甲酰胺 在 sodium methylate 、 甲醇 、 乙醇 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以provided 4.5 g的产率得到1-β-D-ribofuranosyl<1,2,4>triazole-3-thiocarboxamide
  参考文献：
  名称：

  Dendranthema plant named ‘Firedance Igloo’

  摘要：

  一种新的独特的菊花属植物品种，名为“Firedance Igloo”，其特点是植株直立、向外扩展和均匀成丘状；自由分枝习性；植株形态密集而丰满；均匀自由地开花；菊花状花序；明亮的灰紫色花瓣；在宾夕法尼亚州大约在9月17日至22日左右自然季节开花；具有良好的园艺表现和耐寒性。

  公开号：

  USPP029835P2

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：——
• US4992426A
  申请人：——

  公开号：US4992426A

  公开（公告）日：1991-02-12
• USRE29835E
  申请人：——

  公开号：USRE29835E

  公开（公告）日：1978-11-14
• 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.
• Dendranthema plant named ‘Firedance Igloo’
  申请人：Vandenberg Cornelis P.

  公开号：USPP029835P2

  公开（公告）日：2018-11-13

  A new and distinct cultivar of Dendranthema plant named ‘Firedance Igloo’, characterized by its upright, outwardly spreading and uniformly mounded plant habit; freely branching habit; dense and full plant form; uniform and freely flowering habit; daisy-type inflorescences; bright greyed purple-colored ray florets; natural season flowering occurs about September 17 to 22 in Pennsylvania; and good garden performance and winter hardiness.

  一种新的独特的菊花属植物品种，名为“Firedance Igloo”，其特点是植株直立、向外扩展和均匀成丘状；自由分枝习性；植株形态密集而丰满；均匀自由地开花；菊花状花序；明亮的灰紫色花瓣；在宾夕法尼亚州大约在9月17日至22日左右自然季节开花；具有良好的园艺表现和耐寒性。