9-(2-oxopropyl)hypoxanthine | 105970-05-6

• 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: 9-(2-oxopropyl)hypoxanthine
• 英文别名: 1-(9h-Hypoxanthin-9-yl)-2-propanone；9-(2-oxopropyl)-1H-purin-6-one
• CAS: 105970-05-6
• 化学式: C₈H₈N₄O₂
• 分子量: 192.177
• InChiKey: VHMSPBINEGEXLY-UHFFFAOYSA-N

物化性质

• 沸点：
  552.0±30.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(2-oxopropyl)hypoxanthine 、 2-溴甲基丙烯酸乙酯 在 溶剂黄146 、 对苯二酚 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 9-((2-甲基-4-亚甲基-5-氧代四氢呋喃-2-基)甲基)次黄嘌呤
  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：

  乙酰氨基嘌呤 在 sodium methylate 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 9-(2-oxopropyl)hypoxanthine
  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).