4-amino-3-β-D-ribofuranosyl-isothiazole-5-carboxylic acid | 156270-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-3-β-D-ribofuranosyl-isothiazole-5-carboxylic acid
• 英文别名: 4-amino-3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-thiazole-5-carboxylic acid
• CAS: 156270-92-7
• 化学式: C₉H₁₂N₂O₆S
• 分子量: 276.27
• InChiKey: WDWISMSVQYLLDV-ZCIQCHDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  174
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-amino-3-β-D-ribofuranosyl-isothiazole-5-carboxylic acid 在 盐酸 、 氨 作用下， 反应 12.0h， 生成 4-amino-3-(2',3'-O-isopropylidene)-β-D-ribofuranosyl-isothiazole-5-carboxamide
  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：

  dimethyl 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-isothiazoledicarboxylate 在 barium dihydroxide 、 Dowex 50W-X₂ (H(+) form) 、 氨 、 溴 、 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.75h， 生成 4-amino-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

文献信息

• Synthesis of Novel Isothiazole and Isothiazolo[4,5-<i>d</i>] Pyrimidine Analogues of the Natural<i>C</i>-Nucleosides Pyrazofurin and the Formycins
  作者：Diederik K. Buffel、Lieven Meerpoel、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1080/15257779408013275

  日期：1994.3

  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.