N⁶-acetyl-9-(2-oxopropyl)adenine | 105970-01-2

• 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: N⁶-acetyl-9-(2-oxopropyl)adenine
• 英文别名: N-(9-(2-oxopropyl)-9H-purin-6-yl)acetamide；N-(9-(2-Oxopropyl)-9H-purin-6-yl)acetamide；N-[9-(2-oxopropyl)purin-6-yl]acetamide
• CAS: 105970-01-2
• 化学式: C₁₀H₁₁N₅O₂
• 分子量: 233.23
• InChiKey: JOBICPZTKKVIPO-UHFFFAOYSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 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：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁶-acetyl-9-(2-oxopropyl)adenine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到1-(6-氨基-9H-嘌呤-9-基)-2-丙酮
  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：

  一氯丙酮 、 乙酰氨基嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以60%的产率得到N⁶-acetyl-9-(2-oxopropyl)adenine
  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

• Regioselective N9 alkylation of purine rings assisted by β-cyclodextrin
  作者：Qian Zhang、Gang Cheng、Yong-Zhen Huang、Gui-Rong Qu、Hong-Ying Niu、Hai-Ming Guo

  DOI：10.1016/j.tet.2012.07.025

  日期：2012.9

  Under the assistance of beta-cyclodextrin, purine was effectively alkylated at N9 together with up to 99% conversion and good to excellent yield using water as the solvent. High regioselectivity-N9/N7 selectivity>99:1 was attributed to the beta-cyclodextrin cavity blocked the N7 of purines ring. (c) 2012 Elsevier Ltd. All rights reserved.