6-chloro-9-isobutyl-9H-purine | 195252-73-4

• 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: 6-chloro-9-isobutyl-9H-purine
• 英文别名: 6-chloro-9-(2-methylpropyl)purine
• CAS: 195252-73-4
• 化学式: C₉H₁₁ClN₄
• 分子量: 210.666
• InChiKey: JWYRNMHMJHCPIS-UHFFFAOYSA-N

物化性质

• 沸点：
  340.2±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-9-isobutyl-9H-purine 在 硒脲 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以54%的产率得到9-isobutyl-1,9-dihydro-6H-purine-6-selenone
  参考文献：
  名称：

  Chemoselective Perfluoromethylation of Thio- and Selenoamides

  摘要：

  A chemo- and regioselective perfluoromethylation using thioamides/selenoamides (prepared one step from corresponding lactams) as starting materials has been discovered. The reaction demonstrated complementary chemoselectivity to the C-H trifluoromethylation of (hetero)arenes as well as remarkable functional group compatibility especially toward radical sensitive olefin-, alkyne-, and arylhalide-bearing substrates. The examples of perfluorothio-/selenolated drug molecules indicated application potential of this strategy in drug modification and drug-analogue preparation.

  DOI：

  10.1021/acs.orglett.0c03241
• 作为产物：
  描述：

  碘代异丁烷 、 6-氯嘌呤 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以42%的产率得到6-chloro-9-isobutyl-9H-purine
  参考文献：
  名称：

  Chemoselective Perfluoromethylation of Thio- and Selenoamides

  摘要：

  A chemo- and regioselective perfluoromethylation using thioamides/selenoamides (prepared one step from corresponding lactams) as starting materials has been discovered. The reaction demonstrated complementary chemoselectivity to the C-H trifluoromethylation of (hetero)arenes as well as remarkable functional group compatibility especially toward radical sensitive olefin-, alkyne-, and arylhalide-bearing substrates. The examples of perfluorothio-/selenolated drug molecules indicated application potential of this strategy in drug modification and drug-analogue preparation.

  DOI：

  10.1021/acs.orglett.0c03241

文献信息

• 6-(Alkylamino)-9-alkylpurines. A New Class of Potential Antipsychotic Agents
  作者：James L. Kelley、R. Morris Bullock、Mark P. Krochmal、Ed W. McLean、James A. Linn、Micheal J. Durcan、Barrett R. Cooper

  DOI：10.1021/jm960662s

  日期：1997.9.1

  A series of 6-(alkylamino)-9-alkylpurines was synthesized and evaluated for the property of antagonizing the behavioral effects in animals of the dopamine agonist apomorphine. This model for identifying potential antipsychotic agents is based on the hypothesis that agents that antagonize apomorphine-induced aggressive behavior in rats and apomorphine-induced climbing in mice, but that do not block stereotyped behavior, could have an antipsychotic effect in humans without producing extrapyramidal side effects. The antiaggressive-behavior activity of lead compound 1 (6-(dimethylamino)-9-(3-phenylalaninamidobenzyl)-9H-purine) was improved 48-fold with 6-(cyclopropylamino)-9-(cyclopropylmethyl)-2-(trifluoromethyl)-9H-purine (80) (po ED50 of 2 mg/kg), which was obtained through an iterative sequence of structure-activity relationship studies that encompassed evaluation of the effects of structure variations at the purine 9-, 6-, and 2-positions. Potency was enhanced with a 9-cyclopropyl group, the duration of action was improved with the 6-(cyclopropylamino) substituent, potency was further enhanced with an N-formyl prodrug, and an agent with reduced cardiovascular effect emerged with the 2-trifluoromethyl purine 80. This potential antipsychotic agent was not developed further due to undesirable effects on the stomach.