2-[[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl]isoindoline-1,3-dione | 184839-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl]isoindoline-1,3-dione
• 英文别名: 2-[[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]isoindole-1,3-dione
• CAS: 184839-42-7
• 化学式: C₁₈H₁₆N₆O₅
• 分子量: 396.362
• InChiKey: RGMKGDJNRIMSJB-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl]isoindoline-1,3-dione 在 一水合肼 、 溶剂黄146 作用下， 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
• 作为产物：
  描述：

  2-((1R,9R,10R)-4-Methyl-5-oxo-8,11-dioxa-2,6-diaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-10-ylmethyl)-isoindole-1,3-dione 在 盐酸 、 sodium azide 、 lithium chloride 作用下， 生成 2-[[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl]isoindoline-1,3-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

• Orzeszko; Vilpo; Vilpo, Pharmazie, 2003, vol. 58, # 3, p. 169 - 172
  作者：Orzeszko、Vilpo、Vilpo、Kaminska

  DOI：——

  日期：——
• 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.