(2-Acetylphenyl) 3-(3,4-dimethoxyphenyl)prop-2-enoate | 162102-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-Acetylphenyl) 3-(3,4-dimethoxyphenyl)prop-2-enoate
• CAS: 162102-39-8
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: DKAFKGZQPRUEDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-Acetylphenyl) 3-(3,4-dimethoxyphenyl)prop-2-enoate 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  具有癌症预防和治疗潜力的苯并吡喃 4-酮的一锅法合成

  摘要：

  描述了新型苯并吡喃-4-酮的一锅合成。在串联反应中，有机碱催化 (RCOCH2COR2)-C-1 在色酮-3-羧酸上的迈克尔加成导致后者的脱羧和吡喃-4-一环开环。当R-1是邻羟基芳基时，随后是色酮-和/或色满酮环闭合所得迈克尔加合物。14 种衍生物的抗氧化测试确定了色满酮 3o-r 的强抗自由基特性（DPPH 测定中为 2.1-3.1 微摩尔 Trolox 当量/微摩尔化合物）。Chromanones 3p 和 3r 以及 2-styrylchromone 3k 在报告基因测定中诱导细胞保护性 Keap1-Nrf2 信号通路方面也最有效（浓度 <3 μ M 时诱导五倍）。在评估抗增殖活性的七种化合物中，3k 和 3r 的活性最高，

  DOI：

  10.1002/ejoc.201501278
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 哌啶 、 吡啶 、 三氯氧磷 作用下， 反应 6.0h， 生成 (2-Acetylphenyl) 3-(3,4-dimethoxyphenyl)prop-2-enoate
  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

• Synthesis and Sar Study of Diarylpentanoid Analogues as New Anti-Inflammatory Agents
  作者：Sze Leong、Siti Faudzi、Faridah Abas、Mohd Aluwi、Kamal Rullah、Lam Wai、Mohd Bahari、Syahida Ahmad、Chau Tham、Khozirah Shaari、Nordin Lajis

  DOI：10.3390/molecules191016058

  日期：——

  A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 µM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 µM and 9.6 ± 0.5 µM, respectively. A structure–activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.

  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。
• 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.
• Analgesic Effect of 5-(3,4-Dihydroxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one in Experimental Animal Models of Nociception
  作者：Nadhirah Kamarudin、Nadia Hisamuddin、Hui Ong、Ahmad Ahmad Azmi、Sze Leong、Faridah Abas、Mohd Sulaiman、Wan Shaik Mossadeq

  DOI：10.3390/molecules23092099

  日期：——

  antinociceptive activities of 5-(3,4-dihydroxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one (DHHPD), a novel synthetic curcuminoid analogue at 0.1, 0.3, 1 and 3 mg/kg (intraperitoneal), through chemical and thermal models of nociception. The effects of DHHPD on the vanilloid and glutamatergic systems were evaluated through the capsaicin- and glutamate-induced paw licking tests. Results showed that DHHPD

  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
• One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential
  作者：Oualid Talhi、Lidia Brodziak-Jarosz、Jana Panning、Barbora Orlikova、Clemens Zwergel、Tzvetomira Tzanova、Stéphanie Philippot、Diana C. G. A. Pinto、Filipe A. Almeida Paz、Clarissa Gerhäuser、Tobias P. Dick、Claus Jacob、Marc Diederich、Denyse Bagrel、Gilbert Kirsch、Artur M. S. Silva

  DOI：10.1002/ejoc.201501278

  日期：2016.2

  A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of (RCOCH2COR2)-C-1 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone- and/or chromanone ring closure of the resulting Michael adducts when R-1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives

  描述了新型苯并吡喃-4-酮的一锅合成。在串联反应中，有机碱催化 (RCOCH2COR2)-C-1 在色酮-3-羧酸上的迈克尔加成导致后者的脱羧和吡喃-4-一环开环。当R-1是邻羟基芳基时，随后是色酮-和/或色满酮环闭合所得迈克尔加合物。14 种衍生物的抗氧化测试确定了色满酮 3o-r 的强抗自由基特性（DPPH 测定中为 2.1-3.1 微摩尔 Trolox 当量/微摩尔化合物）。Chromanones 3p 和 3r 以及 2-styrylchromone 3k 在报告基因测定中诱导细胞保护性 Keap1-Nrf2 信号通路方面也最有效（浓度 <3 μ M 时诱导五倍）。在评估抗增殖活性的七种化合物中，3k 和 3r 的活性最高，