Thiamiprine 2'-deoxyriboside | 61552-42-9

• 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: Thiamiprine 2'-deoxyriboside
• 英文别名: NSC172614；(2R,3S,5R)-5-[2-amino-6-(3-methyl-5-nitroimidazol-4-yl)sulfanylpurin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 61552-42-9
• 化学式: C₁₄H₁₆N₈O₅S
• 分子量: 408.398
• InChiKey: VQKNUOXJMSCJLJ-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  208
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  beta-胸苷 、 硝咪硫鸟嘌呤 在 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 potassium acetate 作用下， 以 乙二醇二甲醚 、 水 、 二甲基亚砜 为溶剂， 以69%的产率得到Thiamiprine 2'-deoxyriboside
  参考文献：
  名称：

  Nucleosides of azathioprine and thiamiprine as antiarthritics

  摘要：

  Azathioprine [Imuran; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-1H-purine] is a widely used immunosuppressive and antiarthritic drug. For the sake of comparison, the riboside, the 2'-deoxyriboside, and the arabinoside of azathioprine and its 2-amino congener, thiamiprine, were prepared by an enzymatic method. In vitro, the cytotoxicities of these aglycons and their nucleosides were similar (ED50 = 0.8-2 microM), except for the arabinosides, which were nontoxic (ED50 greater than 100 microM). In vivo, their activities were compared in the rat adjuvant arthritis model. The ribosides and 2'-deoxyribosides were less potent than their corresponding aglycons. The safety indexes of these nucleosides were comparable to those of the corresponding aglycons except for the 2'-deoxyriboside of azathioprine, which had an appreciably lower safety index than did azathioprine. Both arabinosides were inactive and nontoxic. All of the aglycons tested (6-mercaptopurine, azathioprine, 6-thioguanine, and thiamiprine) were of similar potency. However, azathioprine had a more favorable therapeutic index than did 6-mercaptopurine. Similarly, thiamiprine was safer than was 6-thioguanine. In this model, the S-(1-methyl-4-nitro-1H-imidazol-5-yl) moiety imparted greater safety to these thiopurines by decreasing toxicity but not affecting potency.

  DOI：

  10.1021/jm00127a013