1-((3aR)-4c-hydroxymethyl-2-oxo-(3ar,6ac)-hexahydro-furo[3,4-d]oxazol-6c-yl)-1H-pyrimidine-2,4-dione | 71120-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((3aR)-4c-hydroxymethyl-2-oxo-(3ar,6ac)-hexahydro-furo[3,4-d]oxazol-6c-yl)-1H-pyrimidine-2,4-dione
• 英文别名: 3'-amino-N,O^2'-carbonyl-3'-deoxy-uridine
• CAS: 71120-26-8
• 化学式: C₁₀H₁₁N₃O₆
• 分子量: 269.214
• InChiKey: XCIZELUYQMZCBN-XVFCMESISA-N

反应信息

• 作为产物：
  描述：

  3'-(3-methyl-3-nitroso-ureido)-3'-deoxy-uridine 在 水 作用下， 生成 1-((3aR)-4c-hydroxymethyl-2-oxo-(3ar,6ac)-hexahydro-furo[3,4-d]oxazol-6c-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Nitrosoureidonucleosides

  摘要：

  3-Deoxyl-1,2-O-isopropylidine-3-(3-methylureido)-alpha-D-ribofuranose (2) was converted to 1,2,5-tri-O-acetyl-3-deoxy-3-(3-acetyl-3-methylureido)-D-ribofuranose (4) and the corresponding glycosyl chloride (7). These sugars were converted to the 3-deoxy-3-(3-methylureido)-beta-D-ribofuranosyl derivatives of adenine (6c), 2-chloroadenine (6d), cytosine (6f), and uracil (6g). Nitrosation of these nucleosides gave the corresponding 3-methyl-3-nitrosoureidonucleosides 8c,d,f,g. 5'-Amino-5'-doxyadenosine (10a), 5'-amino-5'-deoxyuridine (10b), and 5'-amino-5'-deoxycytidine (10c) were all converted to the corresponding 5'-(methylureido)-5'-deoxynucleosides 15a--c by reaction with methyl isocyanate. Nitrosation of these compounds gave the methylnitrosoureidonucleosides 16a--c. These nitrosoureas, potential active-site-directed irreversible enzyme inhibitors, showed little cytotoxicity or activity against leukemia L1210 in vivo.

  DOI：

  10.1021/jm00195a020