2,4-dihydro-4-(β-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one | 80049-45-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dihydro-4-(β-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one
• 英文别名: 4-β-D-Ribofuranosyl-1,2,4-triazol-3(2H)-one；4-β-D-ribofuranosyl-1,2,4-triazolin-3-one；2,4-Dihydro-4-(beta-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one；4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazol-5-one
• CAS: 80049-45-2
• 化学式: C₇H₁₁N₃O₅
• 分子量: 217.181
• InChiKey: ZAVXIBWBPKHKGY-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-dihydro-4-(β-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one 在 四氮唑 、 Oxone 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Phosphoric acid dibenzyl ester (2R,3S,4R,5R)-3,4-dihydroxy-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Ribofuranosyl Triazolone:  A Natural Product Herbicide with Activity on Adenylosuccinate Synthetase Following Phosphorylation

  摘要：

  2,4-Dihydro-4-(beta-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one (2) was identified as the principal phytotoxic component of a fermentation broth derived from an Actinomadura. The compound is a new natural product, but known by synthesis. Broad-spectrum herbicidal activity was demonstrated in greenhouse tests. Metabolite reversal studies suggested the target site was adenylosuccinate synthetase, which was confirmed by direct measurement of the activity of the 5'-phosphorylated derivative on the isolated enzyme.

  DOI：

  10.1021/np990590i
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 盐酸 、 甲酸 、 氨 、 肼 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 124.08h， 生成 2,4-dihydro-4-(β-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one
  参考文献：
  名称：

  Syntheses and structure assignments of six azolinone ribonucleosides

  摘要：

  DOI：

  10.1021/jo00342a020

文献信息

• Hrebabecky, Hubert; Beranek, Jiri, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 2, p. 779 - 788
  作者：Hrebabecky, Hubert、Beranek, Jiri

  DOI：——

  日期：——
• Syntheses and structure assignments of six azolinone ribonucleosides
  作者：David R. Haines、Nelson J. Leonard、David F. Wiemer

  DOI：10.1021/jo00342a020

  日期：1982.1
• Ribofuranosyl Triazolone:  A Natural Product Herbicide with Activity on Adenylosuccinate Synthetase Following Phosphorylation
  作者：Paul R. Schmitzer、Paul R. Graupner、Eleanor L. Chapin、Steven C. Fields、Jeff R. Gilbert、Jim A. Gray、Cathy L. Peacock、B. Clifford Gerwick

  DOI：10.1021/np990590i

  日期：2000.6.1

  2,4-Dihydro-4-(beta-D-ribofuranosyl)-1,2,4(3H)-triazol-3-one (2) was identified as the principal phytotoxic component of a fermentation broth derived from an Actinomadura. The compound is a new natural product, but known by synthesis. Broad-spectrum herbicidal activity was demonstrated in greenhouse tests. Metabolite reversal studies suggested the target site was adenylosuccinate synthetase, which was confirmed by direct measurement of the activity of the 5'-phosphorylated derivative on the isolated enzyme.