5-(6-amino-9H-purin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one | 1311378-31-0

• 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: 5-(6-amino-9H-purin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
• 英文别名: [6]-zingerine；5-(6-Aminopurin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one；5-(6-aminopurin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
• CAS: 1311378-31-0
• 化学式: C₂₂H₂₉N₅O₃
• 分子量: 411.504
• InChiKey: LUSPFIWBBARJFS-UHFFFAOYSA-N

物化性质

• 沸点：
  635.8±65.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-姜烯酚 、 腺嘌呤 在 caesium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以36%的产率得到5-(6-amino-9H-purin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
  参考文献：
  名称：

  Identification of unprecedented purine-containing compounds, the zingerines, from ginger rhizomes (Zingiber officinale Roscoe) using a phase-trafficking approach

  摘要：

  Three unprecedented purine-containing compounds, named [6]-, [8]-, and [10]-zingerines as they are 5-(6-amino-9H-purin-9-yl) analogs of [6]-, [8]-, and [10]-gingerols, respectively, were isolated from a methanolic extract of ginger rhizomes using a phase trafficking-based method that utilizes solid phase reagents allowing for fast and selective simultaneous separation of basic, acidic, and neutral components of natural products extracts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.03.007

文献信息

• Synthesis, molecular docking and Brugia malayi thymidylate kinase (BmTMK) enzyme inhibition study of novel derivatives of [6]-shogaol
  作者：Vinay Kr Singh、Pawan K. Doharey、Vikash Kumar、J.K. Saxena、M.I. Siddiqi、Sushma Rathaur、Tadigoppula Narender

  DOI：10.1016/j.ejmech.2015.01.035

  日期：2015.3

  [6]-Shogaol (1) was isolated from Zingiber officinale. Twelve novel compounds have been synthesized and evaluated for their Brugia malayi thymidylate kinase (BmTMK) inhibition activity, which plays important role for the DNA synthesis in parasite. [6]-Shogaol (1) and shogaol with thymine head group (2), 5-bromouracil head group (3), adenine head group (4) and 2-amino-3-methylpyridine head group (5) showed potential inhibitory effect on BmTMK activity. Further molecular docking studies were carried out to explore the putative binding mode of compounds 1-5. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Identification of unprecedented purine-containing compounds, the zingerines, from ginger rhizomes (Zingiber officinale Roscoe) using a phase-trafficking approach
  作者：Juan J. Araya、Huaping Zhang、Thomas E. Prisinzano、Lester A. Mitscher、Barbara N. Timmermann

  DOI：10.1016/j.phytochem.2011.03.007

  日期：2011.6

  Three unprecedented purine-containing compounds, named [6]-, [8]-, and [10]-zingerines as they are 5-(6-amino-9H-purin-9-yl) analogs of [6]-, [8]-, and [10]-gingerols, respectively, were isolated from a methanolic extract of ginger rhizomes using a phase trafficking-based method that utilizes solid phase reagents allowing for fast and selective simultaneous separation of basic, acidic, and neutral components of natural products extracts. (C) 2011 Elsevier Ltd. All rights reserved.