3-(4-hydroxybenzoyl)-8-methylcoumarin | 1448688-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-hydroxybenzoyl)-8-methylcoumarin
• 英文别名: 3-(4-Hydroxybenzoyl)-8-methylchromen-2-one；3-(4-hydroxybenzoyl)-8-methylchromen-2-one
• CAS: 1448688-13-8
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: SCFBOKOYJISUJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-methyl-3-(4-methoxybenzoyl)coumarin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以56%的产率得到3-(4-hydroxybenzoyl)-8-methylcoumarin
  参考文献：
  名称：

  Synthesis and Electrochemical and Biological Studies of Novel Coumarin–Chalcone Hybrid Compounds

  摘要：

  A series of novel hydroxy-coumarin chalcone hybrid compounds 2a-i has been synthesized by employing a simple and efficient methodology. An electrochemical characterization using cyclic voltammetry and ESR spectroscopy were carried out to characterize the oxidation mechanism for the target compounds. The antioxidant capacity and reactivity were determined by ORAC and ESR assays, respectively. Biological assays were assessed to evaluate the cytotoxicity and cytoprotection capacity against ROS/RNS on BAEC. The results revealed that all tested compounds present ORAC values that are much higher than other well-known antioxidant compounds such as quercetin and catechin. Compound 2e showed the highest ORAC value (14.1) and also presented a low oxidation potential, good scavenging capacity against hydroxyl radicals, low cytotoxicity, and high cytoprotective activity.

  DOI：

  10.1021/jm400546y

文献信息

• Synthesis and Electrochemical and Biological Studies of Novel Coumarin–Chalcone Hybrid Compounds
  作者：Fernanda Pérez-Cruz、Saleta Vazquez-Rodriguez、Maria João Matos、Alejandra Herrera-Morales、Frederick A. Villamena、Amlan Das、Bhavani Gopalakrishnan、Claudio Olea-Azar、Lourdes Santana、Eugenio Uriarte

  DOI：10.1021/jm400546y

  日期：2013.8.8

  A series of novel hydroxy-coumarin chalcone hybrid compounds 2a-i has been synthesized by employing a simple and efficient methodology. An electrochemical characterization using cyclic voltammetry and ESR spectroscopy were carried out to characterize the oxidation mechanism for the target compounds. The antioxidant capacity and reactivity were determined by ORAC and ESR assays, respectively. Biological assays were assessed to evaluate the cytotoxicity and cytoprotection capacity against ROS/RNS on BAEC. The results revealed that all tested compounds present ORAC values that are much higher than other well-known antioxidant compounds such as quercetin and catechin. Compound 2e showed the highest ORAC value (14.1) and also presented a low oxidation potential, good scavenging capacity against hydroxyl radicals, low cytotoxicity, and high cytoprotective activity.