6-bromo-8-hydroxy-3-(3,4-dihydroxybenzoyl)coumarin | 1448688-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-8-hydroxy-3-(3,4-dihydroxybenzoyl)coumarin
• 英文别名: 6-bromo-3-(3’,4’-dihydroxybenzoyl)-8-hydroxycoumarin；6-Bromo-3-(3,4-dihydroxybenzoyl)-8-hydroxychromen-2-one；6-bromo-3-(3,4-dihydroxybenzoyl)-8-hydroxychromen-2-one
• CAS: 1448688-17-2
• 化学式: C₁₆H₉BrO₆
• 分子量: 377.148
• InChiKey: OJNJAUWCSKAHHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-bromo-8-methoxy-3-(3,4-dimethoxybenzoyl)coumarin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以69%的产率得到6-bromo-8-hydroxy-3-(3,4-dihydroxybenzoyl)coumarin
  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 of coumarin–chalcone hybrids and evaluation of their antioxidant and trypanocidal properties
  作者：Saleta Vazquez-Rodriguez、Roberto Figueroa-Guíñez、Maria João Matos、Lourdes Santana、Eugenio Uriarte、Michel Lapier、Juan Diego Maya、Claudio Olea-Azar

  DOI：10.1039/c3md00025g

  日期：——

  Based on the observed biological activities of coumarins and chalcones, we have synthesized coumarin–chalcone hybrids with the aim of evaluating their antioxidant properties and trypanocidal activity against Trypanosoma cruzi, the parasite responsible for Chagas disease. All derivatives have been proved to be good antioxidants in spite of their moderate trypanocidal activity in the epimastigote stage (clone Dm28c). Based on these results, we can conclude that compounds 4 and 5 are potential candidates for in vitro studies of their antioxidant activity. These preliminary findings encourage us to the future structural optimization of these kinds of compounds.

  根据对香豆素和查尔酮的生物活性的观察，我们合成了香豆素-查尔酮杂化物，旨在评估其抗氧化性质以及对导致查加斯病的寄生虫克鲁斯锥虫的杀虫活性。尽管所有衍生物在表裂体阶段（克隆Dm28c）的杀虫活性较为温和，但它们被证明是良好的抗氧化剂。基于这些结果，我们可以得出结论，化合物4和5是进行其抗氧化活性体外研究的潜在候选者。这些初步发现鼓励我们未来对这类化合物进行结构优化。