1-[(2R,4S,5R)-5-(aminomethyl)-4-azidooxolan-2-yl]-5-methylpyrimidine-2,4-dione | 143529-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,4S,5R)-5-(aminomethyl)-4-azidooxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 143529-00-4
• 化学式: C₁₀H₁₄N₆O₃
• 分子量: 266.26
• InChiKey: QTTAJQOPTZRGIG-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-(aminomethyl)-4-azidooxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 氢气 、 溶剂黄146 作用下， 生成 1-[(2R,3S,5R)-2-(aminomethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]-3-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]thiourea
  参考文献：
  名称：

  Replacement of the Negative Phosphodiester Linkages of DNA by Positive S-Methylthiourea Linkers:  A Novel Approach to Putative Antisense Agents

  摘要：

  DOI：

  10.1021/ja980629q
• 作为产物：
  描述：

  beta-胸苷 在 盐酸 、 sodium azide 、 偶氮二甲酸二异丙酯 、 一水合肼 、 溶剂黄146 、 三苯基膦 、 lithium chloride 作用下， 反应 25.0h， 生成 1-[(2R,4S,5R)-5-(aminomethyl)-4-azidooxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  A rapid synthesis of some 5′-amino- nucleosides and nucleotides as potential antiviral compounds

  摘要：

  We describe a convenient method for the synthesis of 5'-amino-3'-azido-3',5'-dideoxythymidine and its conversion to a 5'-blocked phosphate derivative. The compounds are evaluated as inhibitors of HIV-1 in vitro, but prove to be poorly effective by comparison to their 5'-oxygen analogues. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00446-5

文献信息

• Solid-Phase Synthesis of Deoxynucleic Guanidine (DNG) Oligomers and Melting Point and Circular Dichroism Analysis of Binding Fidelity of Octameric Thymidyl Oligomers with DNA Oligomers
  作者：Barry A. Linkletter、Istvan E. Szabo、Thomas C. Bruice

  DOI：10.1021/ja984212w

  日期：1999.4.1

  A practical solid-phase synthesis of deoxynucleic guanidine (DNG), a positively charged DNA backbone analogue, is reported. The nucleoside coupling step in the solid-phase synthesis of DNG involves the attack of a terminal 3‘-amine upon an electronically activated 5‘-carbodiimide to create a protected guanidinium internucleoside linkage. The activated carbodiimide is synthesized in situ by the mercury(II)

  报道了一种实用的固相合成脱氧核胍 (DNG)，一种带正电荷的 DNA 骨架类似物。DNG 固相合成中的核苷偶联步骤涉及末端 3'-胺对电子激活的 5'-碳二亚胺的攻击，以产生受保护的胍核苷间键。活性碳二亚胺是通过汞 (II) 从不对称取代的硫脲中提取硫而原位合成的，其中一个取代基是吸电子保护基团，另一个是 5'-核苷单体。除了碳化二亚胺之外，这还会产生硫化汞沉淀物，该沉淀物积聚在固体载体的孔中，限制溶剂和试剂的进入并降低每个连续循环的偶联产率。这一障碍通过一个简单的洗涤步骤来克服，该步骤涉及一种苯硫酚溶液，该溶液很容易去除汞盐。将这一步添加到循环中使 DNG 低聚物能够合成...
• Synthesis of the Polycation Thymidyl DNG, Its Fidelity in Binding Polyanionic DNA/RNA, and the Stability and Nature of the Hybrid Complexes
  作者：Robert O. Dempcy、Kenneth A. Browne、Thomas C. Bruice

  DOI：10.1021/ja00127a035

  日期：1995.6
• US6136965A
  申请人：——

  公开号：US6136965A

  公开（公告）日：2000-10-24
• Replacement of the Negative Phosphodiester Linkages of DNA by Positive <i>S</i>-Methylthiourea Linkers:  A Novel Approach to Putative Antisense Agents
  作者：Dev P. Arya、Thomas C. Bruice

  DOI：10.1021/ja980629q

  日期：1998.7.1
• A rapid synthesis of some 5′-amino- nucleosides and nucleotides as potential antiviral compounds
  作者：Christopher McGuigan、Stephen Turner、Naheed Mahmood、Alan J Hay

  DOI：10.1016/0960-894x(96)00446-5

  日期：1996.10

  We describe a convenient method for the synthesis of 5'-amino-3'-azido-3',5'-dideoxythymidine and its conversion to a 5'-blocked phosphate derivative. The compounds are evaluated as inhibitors of HIV-1 in vitro, but prove to be poorly effective by comparison to their 5'-oxygen analogues. Copyright (C) 1996 Elsevier Science Ltd.