Azathioprine 2'-deoxyriboside | 116019-33-1

• 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 2'-deoxyriboside
• 英文别名: 9-(β-D-2'-deoxyribofuranosyl)-6-<(1-methyl-4-nitroimidazo-5-yl)thio>purine；(2R,3S,5R)-2-(hydroxymethyl)-5-[6-(3-methyl-5-nitroimidazol-4-yl)sulfanylpurin-9-yl]oxolan-3-ol
• CAS: 116019-33-1
• 化学式: C₁₄H₁₅N₇O₅S
• 分子量: 393.383
• InChiKey: GOHXCDJVHOSNJN-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 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：
  182
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(2R,3S,5R)-5-[6-(3-methyl-5-nitroimidazol-4-yl)sulfanylpurin-9-yl]-3-(4-nitrobenzoyl)oxyoxolan-2-yl]methyl 4-nitrobenzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以50%的产率得到Azathioprine 2'-deoxyriboside
  参考文献：
  名称：

  Mishra, Anil; Pratap, Ram; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 847 - 850

  摘要：

  DOI：

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.
• MISHRA, ANIL;PRATAP, RAM;BHAKUNI, D. S., INDIAN J. CHEM., 26,(1987) N 9, 847-856
  作者：MISHRA, ANIL、PRATAP, RAM、BHAKUNI, D. S.

  DOI：——

  日期：——
• Mishra, Anil; Pratap, Ram; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 847 - 850
  作者：Mishra, Anil、Pratap, Ram、Bhakuni, D. S.

  DOI：——

  日期：——