5'-amino-5'-deoxyadenosine hydrochloride | 4137-54-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-amino-5'-deoxyadenosine hydrochloride
• 英文别名: 5'-aminoadenosine hydrochloride；(2R,3S,4R,5R)-2-(aminomethyl)-5-(6-aminopurin-9-yl)oxolane-3,4-diol;hydrochloride
• CAS: 4137-54-6
• 化学式: C₁₀H₁₄N₆O₃*ClH
• 分子量: 302.721
• InChiKey: WPCMUJNSKWWFSY-MCDZGGTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.59
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-amino-5'-deoxyadenosine hydrochloride 在 三氯硫磷 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 C₁₀H₁₃N₆O₅PS^(2-)
  参考文献：
  名称：

  Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing

  摘要：

  我们最近报道了使用PSCl3对烷基胺进行硫代膦酰化反应，得到的N-硫代膦酰胺离子可以容易地进行S-烷基化（《化学通讯》，2011年，第47卷，第6156-6158页）。在此，我们报道了利用氨基酸、氨基糖、氨基核苷和苯胺底物开发这种方法。研究了N-硫代膦酰胺离子的水解性质及其对烷基化剂的反应活性。此外，我们还展示了该方法在制备小规模化合物库中的应用，其中包括了用于抗利什曼活性测试的喹啉基N,S-二烷基硫代膦酰胺。

  DOI：

  10.1039/c3ob27448a
• 作为产物：
  描述：

  5'-O-(苄基磺酰基)-2',3'-O-异亚丙基腺苷 在 Ra-Ni 叠氮化锂 、 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.25h， 生成 5'-amino-5'-deoxyadenosine hydrochloride
  参考文献：
  名称：

  A new synthetic use of nucleoside N1-oxides

  摘要：

  DOI：

  10.1021/jo01293a005

文献信息

• NAD-based inhibitors with anticancer potential
  作者：Krzysztof Felczak、Robert Vince、Krzysztof W. Pankiewicz

  DOI：10.1016/j.bmcl.2013.11.005

  日期：2014.1

  Three classes of novel inhibitors of inosine monophosphate dehydrogenase have been prepared and their anti-proliferative properties were evaluated against several cancer cell lines.(1) Mycophenolic adenine dinucleotide analogues (8-13) containing a substituent at the C2 of adenine ring were found to be potent inhibitors of IMPDH (K-i's in range of 0.6-82 nM) and sub-mu M inhibitors of leukemic K562 cell proliferation. (2) Mycophenolic adenosine (D and L) esters (20 and 21) showed a potent inhibition of IMPDH2 (K-i = 102 and K-i = 231 nM, respectively) and inhibition of K562 cell growth (IC50 = 0.5 and IC50 = 1.6 mu M). These compounds serve both as inhibitors of the enzyme and as a depot form of mycophenolic acid. The corresponding amide analogue 22, also a potent inhibitor of IMPDH (K-i = 84 nM), did not inhibit cancer cell proliferation. (3) Mycophenolic-(L)-and (D)-valine adenine diamide derivatives 25 (K-i = 9 nM) and 28 (K-i = 3 nM) were found to be very potent enzymatically, but did not inhibit proliferation of cancer cells. (C) 2013 Elsevier Ltd. All rights reserved.
• Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
  作者：Milena Trmčić、Frances L. Chadbourne、Paul M. Brear、Paul W. Denny、Steven L. Cobb、David R. W. Hodgson

  DOI：10.1039/c3ob27448a

  日期：——

  We recently reported the use of PSCl3 for the thiophosphorylation of alkylamines where the resulting N-thiophosphoramidate ions could be readily S-alkylated (Chem. Commun., 2011, 47, 6156–6158.). Herein we report the development of this methodology using amino acid, amino sugar, aminonucleoside and aniline substrates. The hydrolysis properties of N-thiophosphoramidate ions and their reactivities towards alkylating agents are also explored. In addition, we demonstrate the application of our approach to the preparation of a small library of compounds, including quinoline-based N,S-dialkylthiophosphoramidates which were tested for antileishmanial activity.

  我们最近报道了使用PSCl3对烷基胺进行硫代膦酰化反应，得到的N-硫代膦酰胺离子可以容易地进行S-烷基化（《化学通讯》，2011年，第47卷，第6156-6158页）。在此，我们报道了利用氨基酸、氨基糖、氨基核苷和苯胺底物开发这种方法。研究了N-硫代膦酰胺离子的水解性质及其对烷基化剂的反应活性。此外，我们还展示了该方法在制备小规模化合物库中的应用，其中包括了用于抗利什曼活性测试的喹啉基N,S-二烷基硫代膦酰胺。
• A new synthetic use of nucleoside N1-oxides
  作者：Malcolm MacCoss、Eung K. Ryu、Robert S. White、Robert L. Last

  DOI：10.1021/jo01293a005

  日期：1980.2