(E)-2-(1-carboxy-2-phenylvinyl)-4,5-dihydroxybenzoic acid | 1449512-84-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(1-carboxy-2-phenylvinyl)-4,5-dihydroxybenzoic acid
• 英文别名: 2-[(E)-1-carboxy-2-phenylethenyl]-4,5-dihydroxybenzoic acid
• CAS: 1449512-84-8
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: ULJDJCKWWIKHIA-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6,7-dimethoxy-1-oxo-3-phenyl-3,4-dihydroisochromene-4-carboxylic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-2-(1-carboxy-2-phenylvinyl)-4,5-dihydroxybenzoic acid
  参考文献：
  名称：

  A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments

  摘要：

  A series of new stilbenes 4a-n e, 5 were synthesized through a novel one-pot Perkin-like reaction between 6,7-dimethoxyhomophthalic anhydride and aromatic aldehydes, followed by treatment with BBr3. This synthesis is straightforward and allows polyhydroxylated cis-stilbenes gathering two well-known pharmacophoric fragments to be obtained in good yields and for short reaction times. The structure of the newly synthesized compounds was established by spectroscopic methods (H-1 NMR, C-13 NMR, IR and HRMS) and the double bond configuration was unequivocally elucidated by means of gated decoupling C-13 NMR spectra and 2D NOESY experiments. Preliminary differentiating screening of their radical scavenging, antibacterial, anti-fungal and tyrosinase inhibitory activity was further performed. The results obtained suggest that the tested compounds possess a triple biological action as potent radical scavengers, antifungal agents and tyrosinase inhibitors in micromolar concentration. The most promising bioactive compound amongst the others was 4a, acting as excellent radical scavenger against DPPH radical (IC50 <= 10 mu M), antifungal agent suppressing the growth of Fusarium graminearum (89% inhibition at 0.17 mu mol/mL), and tyrosinase inhibitor showing higher activity than hydroquinone at (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.040

文献信息

• A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments
  作者：Mitko Miliovsky、Ivan Svinyarov、Yavor Mitrev、Yana Evstatieva、Dilyana Nikolova、Maya Chochkova、Milen G. Bogdanov

  DOI：10.1016/j.ejmech.2013.05.040

  日期：2013.8

  A series of new stilbenes 4a-n e, 5 were synthesized through a novel one-pot Perkin-like reaction between 6,7-dimethoxyhomophthalic anhydride and aromatic aldehydes, followed by treatment with BBr3. This synthesis is straightforward and allows polyhydroxylated cis-stilbenes gathering two well-known pharmacophoric fragments to be obtained in good yields and for short reaction times. The structure of the newly synthesized compounds was established by spectroscopic methods (H-1 NMR, C-13 NMR, IR and HRMS) and the double bond configuration was unequivocally elucidated by means of gated decoupling C-13 NMR spectra and 2D NOESY experiments. Preliminary differentiating screening of their radical scavenging, antibacterial, anti-fungal and tyrosinase inhibitory activity was further performed. The results obtained suggest that the tested compounds possess a triple biological action as potent radical scavengers, antifungal agents and tyrosinase inhibitors in micromolar concentration. The most promising bioactive compound amongst the others was 4a, acting as excellent radical scavenger against DPPH radical (IC50 <= 10 mu M), antifungal agent suppressing the growth of Fusarium graminearum (89% inhibition at 0.17 mu mol/mL), and tyrosinase inhibitor showing higher activity than hydroquinone at (C) 2013 Elsevier Masson SAS. All rights reserved.