1-(β-D-glucopyranosyl)-5-(trimethylsilyl)ethynylcytosine | 1423627-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-glucopyranosyl)-5-(trimethylsilyl)ethynylcytosine
• 英文别名: 4-amino-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-(2-trimethylsilylethynyl)pyrimidin-2-one
• CAS: 1423627-74-0
• 化学式: C₁₅H₂₃N₃O₆Si
• 分子量: 369.45
• InChiKey: JWFUBZXSWVFPCG-YGEZULPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.97
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(β-D-glucopyranosyl)-5-(trimethylsilyl)ethynylcytosine 在 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以80%的产率得到1-(β-D-glucopyranosyl)-5-ethynylcytosine
  参考文献：
  名称：

  Rapid microwave-enhanced synthesis of C5-alkynyl pyranonucleosides as novel cytotoxic antitumor agents

  摘要：

  A microwave-assisted, one-pot, coupling reaction for the synthesis of C5-alkynyl-uracil and cytosine glucopyranonucleosides has been developed. The reaction is carried out under standard Sonogashira coupling conditions from glucopyranonucleosides of 5-iodouracil or 5-iodocytosine and various terminal alkynes. All compounds were evaluated for their cytostatic and antiviral activity. The 5-phenylethynyluracil pyranonucleoside derivative 6a showed the most promising cytostatic activity (50% inhibitory concentration in the lower micromolar range). No meaningful antiviral activity was recorded. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.092
• 作为产物：
  描述：

  1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)5-iodocytosine 在 copper(l) iodide 、 四(三苯基膦)钯 、 氨 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.05h， 生成 1-(β-D-glucopyranosyl)-5-(trimethylsilyl)ethynylcytosine
  参考文献：
  名称：

  Rapid microwave-enhanced synthesis of C5-alkynyl pyranonucleosides as novel cytotoxic antitumor agents

  摘要：

  A microwave-assisted, one-pot, coupling reaction for the synthesis of C5-alkynyl-uracil and cytosine glucopyranonucleosides has been developed. The reaction is carried out under standard Sonogashira coupling conditions from glucopyranonucleosides of 5-iodouracil or 5-iodocytosine and various terminal alkynes. All compounds were evaluated for their cytostatic and antiviral activity. The 5-phenylethynyluracil pyranonucleoside derivative 6a showed the most promising cytostatic activity (50% inhibitory concentration in the lower micromolar range). No meaningful antiviral activity was recorded. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.092

文献信息

• Rapid microwave-enhanced synthesis of C5-alkynyl pyranonucleosides as novel cytotoxic antitumor agents
  作者：Athina Dimopoulou、Stella Manta、Christos Kiritsis、Dimitra-Niki Gkaragkouni、Ioannis Papasotiriou、Jan Balzarini、Dimitri Komiotis

  DOI：10.1016/j.bmcl.2012.12.092

  日期：2013.3

  A microwave-assisted, one-pot, coupling reaction for the synthesis of C5-alkynyl-uracil and cytosine glucopyranonucleosides has been developed. The reaction is carried out under standard Sonogashira coupling conditions from glucopyranonucleosides of 5-iodouracil or 5-iodocytosine and various terminal alkynes. All compounds were evaluated for their cytostatic and antiviral activity. The 5-phenylethynyluracil pyranonucleoside derivative 6a showed the most promising cytostatic activity (50% inhibitory concentration in the lower micromolar range). No meaningful antiviral activity was recorded. (C) 2013 Elsevier Ltd. All rights reserved.