6-(2-phenethyl)purine | 54108-66-6

• 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-(2-phenethyl)purine
• 英文别名: 6-Phenetylpurine；6(β-Phenethyl)purin；6-phenethyl-7(9)H-purine；6-(2-phenylethyl)-7H-purine
• CAS: 54108-66-6
• 化学式: C₁₃H₁₂N₄
• 分子量: 224.265
• InChiKey: GJDDUSLBIFJFNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 盐酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 28.0h， 生成 6-(2-phenethyl)purine
  参考文献：
  名称：

  Antioxidant activity of synthetic cytokinin analogues: 6-alkynyl- and 6-alkenylpurines as novel 15-Lipoxygenase inhibitors

  摘要：

  Synthetic cytokinin analogues as well as the well known CKs 6-benzylaminopurine (BAP), kinetin and trans-zeatin were examined for antioxidant activity. The compounds were tested as potential diphenylpicrylhydrazyl (DPPH) scavengers and as inhibitors of 15-lipoxygenase (15-LO). The natural plant hormones were essentially inactive in both assays, but several synthetic analogues have a profound inhibiting effect on 15-lipoxygenase from soybeans. The same compounds were only weak DPPH scavengers and they may therefore be regarded as so-called non antioxidant inhibitors of 15-LO. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00427-8

文献信息

• Synthesis of 6-Alkylpurine Derivatives by Nickel-complex-catalyzed Coupling Reaction of 6-(Methylthio)purine Derivatives with Grignard Reagents
  作者：Hideyuki Sugimura、Hisashi Takei

  DOI：10.1246/bcsj.58.664

  日期：1985.2

  CH3(CH2)nCH2 (n=2 to 6), C6H5CH2CH2, (CH3)2 C=CHCH2CH2) in the presence of 5 mol% [NiCl2(Ph2PCH2CH2CH2PPh2)] in refluxing THF for 8 h to afford 6-aryl or 6-alkylpurines in 62–74% yields. By applying this reaction to 6-(methylthio)purine nucleoside, 6-(4-methyl-3-pentenyl)-9-β-D-ribofuranosylpurine was synthesized.

  6-(甲硫基)嘌呤与 RMgX (R=C6H5, CH3(CH2)nCH2 (n=2 to 6), C6H5CH2CH2, (CH3)2 C=CHCH2CH2) 在 5 mol% [NiCl2(Ph2PCH2CH2CH2PPh2)] 存在下反应将 THF 回流 8 小时，以 62-74% 的产率得到 6-芳基或 6-烷基嘌呤。通过将该反应应用于 6-(甲硫基)嘌呤核苷，合成了 6-(4-甲基-3-戊烯基)-9-β-D-呋喃核糖基嘌呤。
• Nishikawa, Shiro; Kumazawa, Zenzaburo; Mizutani, Hiroyuki, Agricultural and Biological Chemistry, 1986, vol. 50, # 4, p. 1089 - 1092
  作者：Nishikawa, Shiro、Kumazawa, Zenzaburo、Mizutani, Hiroyuki、Kashimura, Naoki

  DOI：——

  日期：——
• Preparation for promoting hair growth
  申请人：Sansho Seiyaku Co., Ltd.

  公开号：EP0540854B1

  公开（公告）日：1998-01-21
• US5656264A
  申请人：——

  公开号：US5656264A

  公开（公告）日：1997-08-12
• Antioxidant activity of synthetic cytokinin analogues: 6-alkynyl- and 6-alkenylpurines as novel 15-Lipoxygenase inhibitors
  作者：Anders Bråthe、Geir Andresen、Lise-Lotte Gundersen、Karl E. Malterud、Frode Rise

  DOI：10.1016/s0968-0896(01)00427-8

  日期：2002.5

  Synthetic cytokinin analogues as well as the well known CKs 6-benzylaminopurine (BAP), kinetin and trans-zeatin were examined for antioxidant activity. The compounds were tested as potential diphenylpicrylhydrazyl (DPPH) scavengers and as inhibitors of 15-lipoxygenase (15-LO). The natural plant hormones were essentially inactive in both assays, but several synthetic analogues have a profound inhibiting effect on 15-lipoxygenase from soybeans. The same compounds were only weak DPPH scavengers and they may therefore be regarded as so-called non antioxidant inhibitors of 15-LO. (C) 2002 Elsevier Science Ltd. All rights reserved.