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 | 129149-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 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
• 英文名称: Oxazofurin
• 英文别名: 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-oxazole-4-carboxamide
• CAS: 129149-89-9
• 化学式: C₉H₁₂N₂O₆
• 分子量: 244.204
• InChiKey: YSRISZVOJDAOFB-DBRKOABJSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  625.0±55.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-benzoyl-2,5-anhydro-D-allonic acid chloride 在 吡啶 、 盐酸 、 ammonium hydroxide 、 次磷酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 45.75h， 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

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：——
• Pharmaceutical Composition For Treatment Of Blood Clotting Disorder
  申请人：Honda Takashi

  公开号：US20090232769A1

  公开（公告）日：2009-09-17

  Disclosed is a pharmaceutical composition for the prevention or treatment of blood clotting disorder which can reduce a burden on a patient. The pharmaceutical composition comprises an effective amount of ribavirin or a derivative thereof or a pharmaceutically acceptable salt of ribavirin or the derivative.
• US8217014B2
  申请人：——

  公开号：US8217014B2

  公开（公告）日：2012-07-10
• Synthesis and antitumor activity of 2-.beta.-D-ribofuranosyloxazole-4-carboxamide (oxazofurin)
  作者：Palmarisa Franchetti、Gloria Cristalli、Mario Grifantini、Loredana Cappellacci、Sauro Vittori、Giuseppe Nocentini

  DOI：10.1021/jm00172a027

  日期：1990.10

  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.