4-carbamoyl-3-β-D-ribofuranosyl-isothiazole-5-carboxylic acid | 156270-91-6

• 英文名称: 4-carbamoyl-3-β-D-ribofuranosyl-isothiazole-5-carboxylic acid
• CAS: 156270-91-6
• 化学式: C₁₀H₁₂N₂O₇S
• 分子量: 304.28
• InChiKey: GAJYODVQMBAJCJ-ZCIQCHDPSA-N

物化性质

• 沸点：
  528.4±50.0 °C(predicted)
• 密度：
  1.785±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.91
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  163.2
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-carbamoyl-3-β-D-ribofuranosyl-isothiazole-5-carboxylic acid 在 盐酸 、 barium dihydroxide 、 溴 作用下， 反应 4.75h， 生成 methyl 4-amino-3-(2',3'-O-isopropylidene)-β-D-ribofuranosyl-isothiazole-5-carboxylate
  参考文献：
  名称：

  Synthesis of Novel Isothiazole and Isothiazolo[4,5-d] Pyrimidine Analogues of the NaturalC-Nucleosides Pyrazofurin and the Formycins

  摘要：

  The cycloaddition of tri-O-benzyl-2,5-anhydro-D-allononitrile-N-sulfide with dimethyl acetylenedicarboxylate or with dimethyl fumarate followed by DDQ oxidation was found to give the benzoyl protected dimethyl 3-beta-D-ribofuranosyl-isothiazoledicarboxylate 10. This compound was converted to C-nucleosides 7a, 8 and 9, analogues of pyrazofurin, oxoformycin B and formycin respectively. Despite their structural similarities they did show neither antiviral nor antitumor activity.

  DOI：

  10.1080/15257779408013275
• 作为产物：
  描述：

  5-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-oxathiazol-2-one 在 Dowex 50W-X₂ (H(+) form) 、 氨 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 氯仿 、 氯苯 为溶剂， 反应 7.25h， 生成 4-carbamoyl-3-β-D-ribofuranosyl-isothiazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis of Novel Isothiazole and Isothiazolo[4,5-d] Pyrimidine Analogues of the NaturalC-Nucleosides Pyrazofurin and the Formycins

  摘要：

  The cycloaddition of tri-O-benzyl-2,5-anhydro-D-allononitrile-N-sulfide with dimethyl acetylenedicarboxylate or with dimethyl fumarate followed by DDQ oxidation was found to give the benzoyl protected dimethyl 3-beta-D-ribofuranosyl-isothiazoledicarboxylate 10. This compound was converted to C-nucleosides 7a, 8 and 9, analogues of pyrazofurin, oxoformycin B and formycin respectively. Despite their structural similarities they did show neither antiviral nor antitumor activity.

  DOI：

  10.1080/15257779408013275