2-chloro-6-(2-methoxyanilino)purine | 204633-45-4

• 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: 2-chloro-6-(2-methoxyanilino)purine
• 英文别名: 2-chloro-N-(2-methoxyphenyl)-9H-purin-6-amine；2-chloro-N-(2-methoxyphenyl)-7H-purin-6-amine
• CAS: 204633-45-4
• 化学式: C₁₂H₁₀ClN₅O
• 分子量: 275.697
• InChiKey: UDSYDQBRCXFWHS-UHFFFAOYSA-N

物化性质

• 熔点：
  258 °C
• 沸点：
  405.8±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻甲氧基苯胺 、 2,6-二氯嘌呤 在 N,N-二异丙基乙胺 、 氨 作用下， 以 正丁醇 、 水 为溶剂， 反应 4.0h， 以64%的产率得到2-chloro-6-(2-methoxyanilino)purine
  参考文献：
  名称：

  Novel potent inhibitors of A. thaliana cytokinin oxidase/dehydrogenase

  摘要：

  The synthesis of a new group of 2-X-6-anilinopurines, including compounds with potential cytokinin-like activities, with various substitutions (X = H, halogen, amino, methylthio or nitro) on the phenyl ring is described. The prepared compounds have been characterized using standard physico-chemical methods, and the influence of individual substituents on biological activity has been compared in three different bioassays, based on the stimulation of tobacco callus growth, retention of chlorophyll in excised wheat leaves and the dark induction of betacyanin synthesis in Amaranthus cotyledons. The biological activity of the prepared compounds was also assessed in receptor assays, in which the ability of the compounds to activate the cytokinin receptors AHK3 and AHK4/CRE1 was studied. Finally, the interactions of the compounds with the Arabidopsis cytokinin oxidase/dehydrogenase AtCKX2 (heterologously expressed) were investigated. Systematic testing led to the identification of two very potent inhibitors of AtCKX2: 2-chloro-6-(3-methoxyphenyl)aminopurine and 2-fluoro-6-(3-methoxyphenyl) aminopurine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.008