N²-acetyl-1-(2-oxopropyl)guanine | 105991-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N²-acetyl-1-(2-oxopropyl)guanine
• 英文别名: N-[6-oxo-1-(2-oxopropyl)-7H-purin-2-yl]acetamide
• CAS: 105991-07-9
• 化学式: C₁₀H₁₁N₅O₃
• 分子量: 249.229
• InChiKey: SGLNQDKQPIDDDF-UHFFFAOYSA-N

物化性质

• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N²-acetyl-1-(2-oxopropyl)guanine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以74%的产率得到1-(2-oxopropyl)guanine
  参考文献：
  名称：

  Antitumor agents. 86. Synthesis and cytotoxicity of .alpha.-methylene-.gamma.-lactone-bearing purines

  摘要：

  alpha-Methylene-gamma-lactones covalently linked to adenine, hypoxanthine, and guanine were synthesized by using the convenient Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper purine ketones. In vitro cytotoxicity data demonstrated that these compounds were active against L-1210 tissue culture cells with 3 being most potent (ED50 = 0.3 microgram/mL).

  DOI：

  10.1021/jm00386a025
• 作为产物：
  描述：

  N-2-乙酰鸟嘌呤 、 一氯丙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以30%的产率得到N²-acetyl-9-(2-oxopropyl)guanine
  参考文献：
  名称：

  Antitumor agents. 86. Synthesis and cytotoxicity of .alpha.-methylene-.gamma.-lactone-bearing purines

  摘要：

  alpha-Methylene-gamma-lactones covalently linked to adenine, hypoxanthine, and guanine were synthesized by using the convenient Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper purine ketones. In vitro cytotoxicity data demonstrated that these compounds were active against L-1210 tissue culture cells with 3 being most potent (ED50 = 0.3 microgram/mL).

  DOI：

  10.1021/jm00386a025

文献信息

• Antitumor agents. 86. Synthesis and cytotoxicity of .alpha.-methylene-.gamma.-lactone-bearing purines
  作者：Kuo-Hsiung Lee、Gregory K. Rice、Iris H. Hall、Venkataraman Amarnath

  DOI：10.1021/jm00386a025

  日期：1987.3

  alpha-Methylene-gamma-lactones covalently linked to adenine, hypoxanthine, and guanine were synthesized by using the convenient Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper purine ketones. In vitro cytotoxicity data demonstrated that these compounds were active against L-1210 tissue culture cells with 3 being most potent (ED50 = 0.3 microgram/mL).