1,3,7-Trimethyl-8-[2-(3-methylphenyl)ethylsulfanyl]purine-2,6-dione | 1415676-50-4

• 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: 1,3,7-Trimethyl-8-[2-(3-methylphenyl)ethylsulfanyl]purine-2,6-dione
• 英文别名: 1,3,7-trimethyl-8-[2-(3-methylphenyl)ethylsulfanyl]purine-2,6-dione
• CAS: 1415676-50-4
• 化学式: C₁₇H₂₀N₄O₂S
• 分子量: 344.437
• InChiKey: QAKWYEOOTHPAOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  咖啡因 在 氯 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 1.0h， 生成 1,3,7-Trimethyl-8-[2-(3-methylphenyl)ethylsulfanyl]purine-2,6-dione
  参考文献：
  名称：

  Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues

  摘要：

  In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl) sulfanyl] caffeine (IC50 = 0.223 mu M) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl] caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[( phenylethyl) sulfanyl] caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 mu M. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl) sulfanyl] caffeine analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.005

文献信息

• Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues
  作者：Samantha Mostert、Wayne Mentz、Anél Petzer、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bmc.2012.10.005

  日期：2012.12

  In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl) sulfanyl] caffeine (IC50 = 0.223 mu M) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl] caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[( phenylethyl) sulfanyl] caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 mu M. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl) sulfanyl] caffeine analogues. (C) 2012 Elsevier Ltd. All rights reserved.