6-vinyluridine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 6-vinyluridine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-ethenylpyrimidine-2,4-dione
• 化学式: C₁₁H₁₄N₂O₆
• 分子量: 270.242
• InChiKey: MLYUDHGUZMPGET-PEBGCTIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene-6-vinyluridine 在 三氟乙酸 作用下， 以88%的产率得到6-vinyluridine
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 6-vinyl- and 6-ethynyluridine and 8-vinyl- and 8-ethynyladenosine

  摘要：

  It is well-known that the introduction of vinyl and ethynyl moieties into nucleosides is of crucial importance for cytostatic, antiviral, or other biological activities. In this study 6- and 8-vinyl-and -ethynyluridine and -adenosine were prepared by a general procedure involving the palladium-catalyzed cross-coupling of trimethylsilylacetylene or vinyltributyltin. The introduction of a vinyl group at C-6 of uridine or an ethynyl group at C-8 of adenosine resulted in nucleoside derivatives showing cytostatic activity against several murine and/or human tumor cell lines. Interestingly, 8-vinyladenosine had pronounced selective inhibitory effects on human (Molt/4F and MT-4) versus murine (L1210 and FM3A) tumor cell lines.

  DOI：

  10.1021/jm00001a025

文献信息

• Synthesis and cytotoxic activity of 6-vinyl- and 6-ethynyluridine and 8-vinyl- and 8-ethynyladenosine
  作者：Stefano Manfredini、Pier G. Baraldi、Rita Bazzanini、Mirella Marangoni、Daniele Simoni、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00001a025

  日期：1995.1

  It is well-known that the introduction of vinyl and ethynyl moieties into nucleosides is of crucial importance for cytostatic, antiviral, or other biological activities. In this study 6- and 8-vinyl-and -ethynyluridine and -adenosine were prepared by a general procedure involving the palladium-catalyzed cross-coupling of trimethylsilylacetylene or vinyltributyltin. The introduction of a vinyl group at C-6 of uridine or an ethynyl group at C-8 of adenosine resulted in nucleoside derivatives showing cytostatic activity against several murine and/or human tumor cell lines. Interestingly, 8-vinyladenosine had pronounced selective inhibitory effects on human (Molt/4F and MT-4) versus murine (L1210 and FM3A) tumor cell lines.