Azathioprine arabinooside | 120416-99-1

• 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: Azathioprine arabinooside
• 英文别名: (2R,3S,4S,5R)-2-(hydroxymethyl)-5-[6-(3-methyl-5-nitroimidazol-4-yl)sulfanylpurin-9-yl]oxolane-3,4-diol
• CAS: 120416-99-1
• 化学式: C₁₄H₁₅N₇O₆S
• 分子量: 409.382
• InChiKey: YGMZALSIUBISJA-LJUQJJLCSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  811.5±75.0 °C(Predicted)
• 密度：
  2.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  203
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  硝咪硫鸟嘌呤 、 Azathioprine arabinooside 生成 尿嘧啶
  参考文献：
  名称：

  KRENITSKY, THOMAS A.;HALL, WILLARD W.;SELPH, JEFFREY L.;TRUAX, JAMES F.;V+, J. MED. CHEM., 32,(1989) N, C. 1471-1475

  摘要：

  DOI：
• 作为产物：
  描述：

  硫唑嘌呤 、 阿糖尿苷 在 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 作用下， 以 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到Azathioprine arabinooside
  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

文献信息

• Nucleosides of azathioprine and thiamiprine as antiarthritics
  作者：Thomas A. Krenitsky、Willard W. Hall、Jeffrey L. Selph、James F. Truax、Ralph Vinegar

  DOI：10.1021/jm00127a013

  日期：1989.7

  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.
• KRENITSKY, THOMAS A.;HALL, WILLARD W.;SELPH, JEFFREY L.;TRUAX, JAMES F.;V+, J. MED. CHEM., 32,(1989) N, C. 1471-1475
  作者：KRENITSKY, THOMAS A.、HALL, WILLARD W.、SELPH, JEFFREY L.、TRUAX, JAMES F.、V+

  DOI：——

  日期：——