N-(1,2-dihydro-1-((2R,4R)-tetrahydro-4-hydroxyfuran-2-yl)-2-oxopyrimidin-4-yl)acetamide | 1333503-77-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1,2-dihydro-1-((2R,4R)-tetrahydro-4-hydroxyfuran-2-yl)-2-oxopyrimidin-4-yl)acetamide
• 英文别名: N-[1-[(2R,4R)-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 1333503-77-7
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: LCBWYRGPOFZIKH-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1,2-dihydro-1-((2R,4R)-tetrahydro-4-hydroxyfuran-2-yl)-2-oxopyrimidin-4-yl)acetamide 在 甲醇 、 氨 作用下， 以67%的产率得到4-amino-1-((2R,4R)-tetrahydro-4-hydroxyfuran-2-yl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

  摘要：

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.036
• 作为产物：
  描述：

  N-(1-((2R,3R,4S)-4-(benzyloxy)-tetrahydro-3-hydroxyfuran-2-yl)-1,2-dihydro-2-oxopyrimidin-4-yl)acetamide 在 4-二甲氨基吡啶 、 对甲苯基氯化亚硫代甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 N-(1,2-dihydro-1-((2R,4R)-tetrahydro-4-hydroxyfuran-2-yl)-2-oxopyrimidin-4-yl)acetamide
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides

  摘要：

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.036

文献信息

• Synthesis and antiviral evaluation of α-l-2′-deoxythreofuranosyl nucleosides
  作者：Kiran S. Toti、Marco Derudas、Christopher McGuigan、Jan Balzarini、Serge Van Calenbergh

  DOI：10.1016/j.ejmech.2011.05.036

  日期：2011.9

  The synthesis of a series of alpha-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-alpha-L-threose, involving a Vorbruggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase. (C) 2011 Elsevier Masson SAS. All rights reserved.