2-(1-hydroxy-6-iminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol | 7013-17-4

• 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: 2-(1-hydroxy-6-iminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• 英文别名: 1-(6-amino-1-oxy-purin-9-yl)-β-D-1-deoxy-xylofuranose
• CAS: 7013-17-4
• 化学式: C₁₀H₁₃N₅O₅
• 分子量: 283.244
• InChiKey: VYSCKHGOLQAMAT-UHTZMRCNSA-N

物化性质

• 熔点：
  245-252 °C(Solv: water (7732-18-5))
• 沸点：
  777.4±70.0 °C(Predicted)
• 密度：
  2.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.74
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  153.59
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  腺苷 生成 2-(1-hydroxy-6-iminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  参考文献：
  名称：

  MATSUXIRO, XIDEHO;KIKUGAVA, KIEMI;ITINO, MOTONOBU

  摘要：

  DOI：

文献信息

• Microbial Synthesis of Purine Arabinosides and Their Biological Activity
  作者：Takashi Utagawa、Hirokazu Morisawa、Shigeru Yamanaka、Akihiro Yamazaki、Fumihiro Yoshinaga、Yoshio Hirose

  DOI：10.1080/00021369.1985.10867042

  日期：1985.7

  A simple method for the synthesis of various purine arabinosides from purine bases and uracil arabinoside by microbial transarabinosylation is described. A wet cell paste of Enterobacter aerogenes AJ 11125 showed a wide substrate specificity range for purine bases. Not only naturally occurring purine bases such as adenine and hypoxanthine but also unnatural bases such as 6-thioguanine and 2-chlorohypoxanthine were catalyzed to give the corresponding purine arabinosides. The enzymatically synthesized purine arabinosides were isolated from the reaction mixtures and identified by physicochemical means. The biological activities of the compounds were investigated and it was found that thioguanine arabinoside and 2-methyladenine arabinoside have potent activity against Hela cells, and their ED50 were 10.5 and 21.5 μg/ml, respectively.

  描述了一种通过微生物反转阿拉伯糖基化法合成各种嘌呤阿拉伯糖苷的简单方法。Enterobacter aerogenes AJ 11125 的湿细胞浆对嘌呤碱具有广泛的底物特异性范围。不仅天然存在的嘌呤碱如腺嘌呤和次黄嘌呤，而且不自然的碱基如6-巯基鸟嘌呤和2-氯次黄嘌呤也被催化生成相应的嘌呤阿拉伯糖苷。酶合成的嘌呤阿拉伯糖苷从反应混合物中分离出来，并通过物理化学方法鉴定。这些化合物的生物活性进行了研究，发现巯基鸟嘌呤阿拉伯糖苷和2-甲基腺嘌呤阿拉伯糖苷对Hela细胞具有强效活性，它们的ED50分别为10.5和21.5 μg/ml。
• Synthesis and Antiviral Evaluation of Analogs of Adenosine-<i>N</i>¹-Oxide and 1-(Benzyloxy)Adenosine
  作者：Cecil D. Kwong、Charles A. Krauth、Anita T. Shortnacy-Fowler、Gussie Arnett、Melinda G. Hollingshead、William M. Shannon、John A. Montgomery、John A. Secrist

  DOI：10.1080/07328319808003478

  日期：1998.8

  The application of recombinant DNA technology to vaccinia virus for the purpose of developing vaccines dates back nearly twenty years. Since that time a number of recombinant vaccinia-based vaccines have been developed for both veterinary(1-16) and human(17-27) use. Recent recombinant vaccinia vaccines for human use have focused on both cancer(18,19,21-24) and AIDS.(25-27) Several. reviews that summarize recent progress with poxvirus-based vaccines are available.(28-33) Over the years various anecdotal complications with vaccinia virus inoculations have been reported,(34-36) and other human safety concerns include potentially serious adverse consequences in immunocompromised individuals, and adverse reactions in a few normal individuals.(28) Other safety concerns relative to genetic changes in the virus also exist.(32) In view of these issues, some years ago the U.S. Army embarked on a program searching for small molecule drugs that could be used for the prevention or treatment of complications associated with the administration of either vaccinia virus itself or a recombinant vector derived from it. This report presents data on a series of compounds that we prepared as a part of that program.(37).