N6-Phenyl-9-methyladenine | 84602-82-4

• 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: N6-Phenyl-9-methyladenine
• 英文别名: 6-Anilino-9-methylpurine；9-methyl-N-phenyl-9H-purin-6-amine；(9-Methyl-9H-purin-6-yl)-phenyl-amine；9-methyl-N-phenylpurin-6-amine
• CAS: 84602-82-4
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: STTSYIXNIOADQX-UHFFFAOYSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  452.0±48.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-氯-9-甲基嘌呤 在 potassium amide 作用下， 以 氨 为溶剂， 反应 2.0h， 生成 N6-Phenyl-9-methyladenine
  参考文献：
  名称：

  Pyrimidines. Part 96. Anion formation and ring opening of 9-substituted purines in liquid ammonia containing potassium amide

  摘要：

  DOI：

  10.1021/jo00154a021

文献信息

• Verwendung von Purinderivaten als selektive Kinase-Inhibitoren
  申请人：MERCKLE GMBH

  公开号：EP1444982A1

  公开（公告）日：2004-08-11

  Die vorliegende Erfindung betrifft die Verwendung von Purinderivaten zur selektiven Inhibierung von Kinasen. Die Verbindungen sind daher zur Behandlung von Erkrankungen brauchbar, welche in Zusammenhang mit der Kinase-Aktivität stehen.

  本发明涉及使用嘌呤衍生物选择性抑制激酶。因此，这些化合物可用于治疗与激酶活性有关的疾病。
• N6,9-Disubstituted adenines: potent, selective antagonists at the A1 adenosine receptor
  作者：Robert D. Thompson、Sherrie Secunda、John W. Daly、Ray A. Olsson

  DOI：10.1021/jm00113a029

  日期：1991.9

  N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors. The present study assessed the effect of N6 and N-9 substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide. The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > methyl > 2-hydroxyethyl. The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor. An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold. The N6-cyclophenyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent. A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.
• Synthesis and Biological Testing of Purine Derivatives as Potential ATP-Competitive Kinase Inhibitors
  作者：Stefan A. Laufer、David M. Domeyer、Thomas R. F. Scior、Wolfgang Albrecht、Dominik R. J. Hauser

  DOI：10.1021/jm0408767

  日期：2005.2.1

  On the basis of ATP adenine, a series of adenine and purine derivatives was prepared and tested for their ability to inhibit a spectrum of disease-related kinases. There has been scant research investigating the potential of cosubstrate derived kinase inhibitors for other kinases than CDKs. Our inhibitor design combined the purine system from the original cosubstrate ATP and phenyl moieties in order to explore possible interactions with the different regions of the ATP binding site in several disease-related protein kinases. There have been a number of hits for the assayed substances, which led us to conclude that the spectrum of compounds may prove to be a valuable tool kit for the evaluation of bonding and selectivity patterns for a wide variety of kinases.
• NIELSEN, K. E.;PEDERSEN, E. B., CHEM. SCR., 1984, 24, N 4-5, 224-229
  作者：NIELSEN, K. E.、PEDERSEN, E. B.

  DOI：——

  日期：——
• Pyrimidines. Part 96. Anion formation and ring opening of 9-substituted purines in liquid ammonia containing potassium amide
  作者：Nico J. Kos、Henk C. Van der Plas、Wouter J. F. Blees

  DOI：10.1021/jo00154a021

  日期：1983.3