6-azauridine 5'-acetate | 10276-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azauridine 5'-acetate
• 英文别名: 5'-acetyl-6-azauridine；2-(O⁵-acetyl-β-D-ribofuranosyl)-2H-[1,2,4]triazine-3,5-dione；2-β-D-ribofuranosyl-as-triazine-3,5(2H,4H)-dione, 5'-acetate；5'-O-Acetyl-6-aza-uridin；6-Azauridine 5'-monoacetate；[(2R,3S,4R,5R)-5-(3,5-dioxo-1,2,4-triazin-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl acetate
• CAS: 10276-30-9
• 化学式: C₁₀H₁₃N₃O₇
• 分子量: 287.229
• InChiKey: QLJBEHSHSIBNES-ZOQUXTDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 6-氮杂尿苷 在 Candida antarctica lipase B 作用下， 以 异辛烷 、 丙酮 为溶剂， 反应 2.5h， 以99%的产率得到6-azauridine 5'-acetate
  参考文献：
  名称：

  Effect of Binary Organic Solvent Mixtures on Lipase-Catalyzed Regioselective Acylation of 6-Azauridine with Various Structural Vinyl Esters

  摘要：

  在本文中，成功地在基于疏水性的二元溶剂系统中使用南极酵母脂肪酶B对6-氮杂尿苷进行区域选择性酰化，以制备其潜在的前药。比较研究表明，使用二元混合溶剂（醋酮与异辛烷按85:15的体积比例）作为反应介质显著改善了酶的反应速率、热稳定性和操作稳定性。此外，酰基供体的结构对酶在二元溶剂系统中的行为具有重要影响，这可能是由于它们与脂肪酶活性位点之间的不同相互作用所致。

  DOI：

  10.14233/ajchem.2014.17850

文献信息

• ——
  作者：C. M. Riley、M. A. Mummert、J. Zhou、R. L. Schowen、D. G. Vander Velde、M. D. Morton、M. Slavik

  DOI：10.1023/a:1016238110533

  日期：——

  Purpose. The purposes were to study the kinetics of hydrolysis of 2',3',5'-triacetyl-6-azauridine (I) in aqueous solution (mu = 0.5) and to identify the main intermediates and products of the reaction. Methods. A stability indicating isocratic LC assay was used to study the rate of degradation of 1. A gradient LC assay was used to study the time courses of the degradants. The products of hydrolysis were isolated by preparative liquid chromatography and identified by H-1-NMR and CI-MS. The pK(a) value was obtained by potentiometric titration. Results. At 36.8 degrees C, the pH-rate profile of I in water was adequately described by a four-term rate equation. The intermediates were identified as the primary and secondary di-acetates, and the primary and secondary mono-acetates. The final product was 6-azauridine. Conclusions. A simplified kinetic scheme could be used to describe the concentration-time profiles of I, the intermediates and the final product.