9-((2-甲基-4-亚甲基-5-氧代四氢呋喃-2-基)甲基)次黄嘌呤 | 100682-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 9-((2-甲基-4-亚甲基-5-氧代四氢呋喃-2-基)甲基)次黄嘌呤
• 英文名称: 5'-methyl-5'-<(6-hydroxy-9H-purin-9-yl)methyl>-2'-oxo-3'-methylenetetrahydrofuran
• 英文别名: 9-((2-Methyl-4-methylene-5-oxotetrahydrofuran-2-yl)methyl)hypoxanthine；9-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-1H-purin-6-one
• CAS: 100682-44-8
• 化学式: C₁₂H₁₂N₄O₃
• 分子量: 260.252
• InChiKey: DKGIDXRLFYRRKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰氨基嘌呤 在 sodium methylate 、 potassium carbonate 、 溶剂黄146 、 对苯二酚 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 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

文献信息

• New .alpha.-methylene .gamma.-lactone derivatives of substituted nucleic acid bases as potential anticancer agents
  作者：Utpal Sanyal、Saktimoyee Mitra、Prasun Pal、S. K. Chakraborti

  DOI：10.1021/jm00155a001

  日期：1986.5
• 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).