5-(3,4-dimethoxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one | 1011791-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3,4-dimethoxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one
• CAS: 1011791-78-8
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: MNGJUHWORXBOGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(3,4-dimethoxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以37.15%的产率得到5-(3,4-dihydroxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one
  参考文献：
  名称：

  5-(3,4-二羟基苯基)-3-羟基-1-(2-羟基苯基)penta-2,4-dien-1-one 在伤害感受实验动物模型中的镇痛作用

  摘要：

  据报道，源自姜黄根茎的类姜黄素具有镇痛、抗氧化和抗炎活性。我们评估了 5-(3,4-dihydroxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one (DHHPD)（一种新型合成类姜黄素类似物）的外周和中枢镇痛活性通过伤害感受的化学和热模型，以 0.1、0.3、1 和 3 mg/kg（腹膜内）给药。DHHPD 对香草素和谷氨酸能系统的影响通过辣椒素和谷氨酸诱导的舔爪试验进行评估。结果表明，DHHPD 显着 (p < 0.05) 减弱了 0.8% 乙酸注射产生的扭体反应。此外，1 和 3 毫克/千克的 DHHPD 显着 (p < 0.05) 减少了每只小鼠在 2 阶段的两个阶段所花费的舔食时间。5%福尔马林试验，增加小鼠对电炉的反应潜伏期。然而，后者产生的作用并没有被非选择性阿片受体拮抗剂纳洛酮逆转。尽管如此，DHHPD 以

  DOI：

  10.3390/molecules23092099
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 在 吡啶 、 potassium hydroxide 、 三氯氧磷 作用下， 生成 5-(3,4-dimethoxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis and Sar Study of Diarylpentanoid Analogues as New Anti-Inflammatory Agents

  摘要：

  合成了97系列二苯基戊烷类化合物，并通过使用γ干扰素（IFN-γ）/脂多糖（LPS）刺激的RAW264.7巨噬细胞进行NO抑制试验评估其抗炎活性。12个化合物（9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88和97）与姜黄素（14.7 ± 0.2 µM）相比显示出更大或相似的NO抑制活性，特别是化合物88和97，它们表现出最显著的NO抑制活性，IC50值分别为4.9 ± 0.3 µM和9.6 ± 0.5 µM。结构-活性关系（SAR）研究表明，两个芳香环上羟基的存在对这些分子的生物活性至关重要。除了多酚类衍生物外，A环上低电子密度和B环上高电子密度对提高NO抑制作用很重要。同时，药效团映射表明，B环上间位和对位上的羟基取代可能是高活性二苯基戊烷类化合物的标记。

  DOI：

  10.3390/molecules191016058

文献信息

• 2,3-Diarylxanthones as strong scavengers of reactive oxygen and nitrogen species: A structure–activity relationship study
  作者：Clementina M.M. Santos、Marisa Freitas、Daniela Ribeiro、Ana Gomes、Artur M.S. Silva、José A.S. Cavaleiro、Eduarda Fernandes

  DOI：10.1016/j.bmc.2010.07.044

  日期：2010.9

  Xanthones are a class of oxygen-containing heterocyclic compounds widely distributed in nature. The natural derivatives can present different substitutions in the xanthone core that include hydroxyl, methoxyl, prenyl and glycosyl groups. The inclusion of aryl groups has only been reported for a few synthetic derivatives, the 2,3-diaryl moiety being recently introduced by our group. Xanthones are endowed with a broad spectrum of biological activities, many of them related to their antioxidant ability, including the scavenging of reactive oxygen species (ROS) and reactive nitrogen species (RNS), as well as metal chelating effects. Considering the interesting and promising antioxidant activities present in compounds derived from the xanthone core, the main goal of this work was to evaluate the scavenging activity of the new 2,3-diarylxanthones for ROS, including superoxide radical (O-2(center dot-)), hydrogen peroxide (H2O2), singlet oxygen (O-1(2)), peroxyl radical (ROO center dot) and hypochlorous acid (HOCl), and RNS, including nitric oxide ((NO)-N-center dot) and peroxynitrite anion (ONOO center dot). The obtained results revealed that the tested 2,3-diarylxanthones are endowed with outstanding ROS and RNS scavenging properties, considering the nanomolar to micromolar range of the IC50 values found. The xanthones with two catechol rings were the most potent scavengers of all tested ROS and RNS. In conclusion, the new 2,3-diarylxanthones are promising molecules to be used for their potential antioxidant properties. (C) 2010 Elsevier Ltd. All rights reserved.