ethyl 5-amino-2-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxazole-4-carboxylate | 129149-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-amino-2-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxazole-4-carboxylate
• 英文别名: ethyl 5-amino-2-[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]-1,3-oxazole-4-carboxylate
• CAS: 129149-85-5
• 化学式: C₃₂H₂₈N₂O₁₀
• 分子量: 600.582
• InChiKey: JSBSGIXQRHOTFA-VNSJUHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  166.48
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-2-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxazole-4-carboxylate 在 盐酸 、 ammonium hydroxide 、 次磷酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.75h， 生成 2-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-1,3-恶唑-4-甲酰胺
  参考文献：
  名称：

  Synthesis and antitumor activity of 2-.beta.-D-ribofuranosyloxazole-4-carboxamide (oxazofurin)

  摘要：

  Condensation of 3,4,6-tri-O-benzoyl-2,5-anhydro-D-allonyl chloride (4) with ethyl 2-amino-2-cyanoacetate (5) provided 2-[(3',4',6'-tri-O-benzoyl-2',5'-anhydroallonyl)amino]-2-cyanoa cetate (6). Compound 6 was treated with hydrogen chloride gas to give ethyl 5-amino-2-(2',3',5'-tri-O-benzoyl-beta-D- ribofuranosyl)oxazole-4-carboxylate (8). Reductive dediazotization of blocked nucleoside 8 provided ethyl 2-(2',3',5'-tri-O- benzoyl-beta-D-ribofuranosyl)oxazole-4-carboxylate (10), which after deblocking with sodium methoxide and ammonolysis was converted to 2-beta-D-ribofuranosyl-oxazole-4-carboxamide (oxazofurin, 3), an analogue of the antitumor and antiviral C-nucleoside tiazofurin (1). Oxazofurin (3) was found to be cytotoxic toward B16 murine melanoma cells in culture but inactive against murine leukemia P388 and L1210.

  DOI：

  10.1021/jm00172a027
• 作为产物：
  描述：

  3,4,6-tri-O-benzoyl-2,5-anhydro-D-allonic acid chloride 在 吡啶 、 盐酸 作用下， 以 丙酮 为溶剂， 反应 35.0h， 生成 ethyl 5-amino-2-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)oxazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of 2-.beta.-D-ribofuranosyloxazole-4-carboxamide (oxazofurin)

  摘要：

  Condensation of 3,4,6-tri-O-benzoyl-2,5-anhydro-D-allonyl chloride (4) with ethyl 2-amino-2-cyanoacetate (5) provided 2-[(3',4',6'-tri-O-benzoyl-2',5'-anhydroallonyl)amino]-2-cyanoa cetate (6). Compound 6 was treated with hydrogen chloride gas to give ethyl 5-amino-2-(2',3',5'-tri-O-benzoyl-beta-D- ribofuranosyl)oxazole-4-carboxylate (8). Reductive dediazotization of blocked nucleoside 8 provided ethyl 2-(2',3',5'-tri-O- benzoyl-beta-D-ribofuranosyl)oxazole-4-carboxylate (10), which after deblocking with sodium methoxide and ammonolysis was converted to 2-beta-D-ribofuranosyl-oxazole-4-carboxamide (oxazofurin, 3), an analogue of the antitumor and antiviral C-nucleoside tiazofurin (1). Oxazofurin (3) was found to be cytotoxic toward B16 murine melanoma cells in culture but inactive against murine leukemia P388 and L1210.

  DOI：

  10.1021/jm00172a027

文献信息

• FRANCHETTI, PALMARISA;CRISTALLI, GLORIA;GRIFANTINI, MARIO;CAPPELLACCI, LO+, J. MED. CHEM., 33,(1990) N0, C. 2849-2852
  作者：FRANCHETTI, PALMARISA、CRISTALLI, GLORIA、GRIFANTINI, MARIO、CAPPELLACCI, LO+

  DOI：——

  日期：——