3'-(3-methyl-ureido)-3'-deoxy-adenosine | 71120-17-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3'-(3-methyl-ureido)-3'-deoxy-adenosine
• 英文别名: 1-[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-methylurea
• CAS: 71120-17-7
• 化学式: C₁₂H₁₇N₇O₄
• 分子量: 323.311
• InChiKey: FZQANPUAYCYHCN-HUKYDQBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  160
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-(3-methyl-ureido)-3'-deoxy-adenosine 在 水 作用下， 生成 (3aR)-6c-(6-amino-purin-9-yl)-4c-hydroxymethyl-(3ar,6ac)-tetrahydro-furo[3,4-d]oxazol-2-one
  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

文献信息

• Nitrosoureidonucleosides
  作者：J. A. Montgomery、H. J. Thomas

  DOI：10.1021/jm00195a020

  日期：1979.9

  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.