7-O-(4''-chlorophenylmethyl)galangin | 1160162-44-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-O-(4''-chlorophenylmethyl)galangin
• 英文别名: 7-[(4-Chlorophenyl)methoxy]-3,5-dihydroxy-2-phenyl-chromen-4-one；7-[(4-chlorophenyl)methoxy]-3,5-dihydroxy-2-phenylchromen-4-one
• CAS: 1160162-44-6
• 化学式: C₂₂H₁₅ClO₅
• 分子量: 394.811
• InChiKey: LNZDUJJGONIHDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-((4-chlorobenzyl)oxy)-4-oxo-2-phenyl-4H-chromene-3,5-diyl diacetate 在 氨 作用下， 以 甲醇 为溶剂， 生成 7-O-(4''-chlorophenylmethyl)galangin
  参考文献：
  名称：

  7-O-Arylmethylgalangin as a novel scaffold for anti-HCV agents

  摘要：

  In spite of potent antiviral activity, suboptimal physicochemical properties of aryl diketo acids (ADKs) necessitates modification of the core 1,3-diketo acid functionality into a novel scaffold. As the metal-binding affinity of the diketo acid is the key to the antiviral activity of ADKs, we anticipated 3,5-dihydroxy-4-oxo arrangement of galangin scaffold would serve as an excellent mimic for the diketo acid functionality. In this study, through synthesis and biological evaluation of various galangin derivatives, we have shown that the diketo acid functionality can be successfully replaced with the galangin scaffold by specific combination of the substituents to result in identification of a novel galangin derivative (3s) with anti-HCV activity (EC50 = 0.9 mu M) comparable to the ADK counterpart. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.012

文献信息

• 7-O-Arylmethylgalangin as a novel scaffold for anti-HCV agents
  作者：Hyo Seon Lee、Kwang-su Park、Chaewoon Lee、Bokhui Lee、Dong-Eun Kim、Youhoon Chong

  DOI：10.1016/j.bmcl.2010.08.012

  日期：2010.10

  In spite of potent antiviral activity, suboptimal physicochemical properties of aryl diketo acids (ADKs) necessitates modification of the core 1,3-diketo acid functionality into a novel scaffold. As the metal-binding affinity of the diketo acid is the key to the antiviral activity of ADKs, we anticipated 3,5-dihydroxy-4-oxo arrangement of galangin scaffold would serve as an excellent mimic for the diketo acid functionality. In this study, through synthesis and biological evaluation of various galangin derivatives, we have shown that the diketo acid functionality can be successfully replaced with the galangin scaffold by specific combination of the substituents to result in identification of a novel galangin derivative (3s) with anti-HCV activity (EC50 = 0.9 mu M) comparable to the ADK counterpart. (C) 2010 Elsevier Ltd. All rights reserved.