1-(3,4,5-trimethoxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one | 153307-52-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3,4,5-trimethoxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
• 英文别名: 3-(3,4-dihydroxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 153307-52-9
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: YRADLNGHQMLFDH-UHFFFAOYSA-N

物化性质

• 沸点：
  553.9±50.0 °C(predicted)
• 密度：
  1.276±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-trimethoxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one 在 palladium 10% on activated carbon 、 氢气 、 乙酸乙酯 作用下， 生成
  参考文献：
  名称：

  3′,4′,5′-trimethoxy- and 3,4-dimethoxychalcones targeting A549 cells: Synthesis, cytotoxic activity, and molecular docking

  摘要：

  DOI：

  10.1016/j.molstruc.2022.134572
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 3,4-二羟基苯甲醛 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 1-(3,4,5-trimethoxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Antimicrobial, Anti-Inflammatory and Antioxidant Activities of Polyoxygenated Chalcones

  摘要：

  It was synthesized nine polyoxygenated chalcones with a potential and safe use as antioxidant, antimicrobial and anti-inflammatory therapies. Chalcones obtained by Claisen-Schmidt condensation were studied as antioxidant, inhibitors of human 5-lipoxygenase, antifungal, antibacterial and antibiotic resistance modifiers. Two chalcones with catecholic moieties were able to strongly decrease the minimum inhibitory concentration (MIC) of methicillin against methicillin-resistant Staphylococcus aureus, increase the antiradical activity and significantly inhibit the human 5-lipoxygenase. Only one of these chalcones was active synergistically with methicillin. Chalcones with methoxyl substituents at different positions displayed the best activities against Cryptococcus neoformans. Only one chalcone showed good activity against the plant pathogenic bacteria Pseudomonas syringae whose half maximal inhibitory concentration (IC50) value (2.5 mu g mL(-1)) was similar to that observed with the antibiotic streptomycin (2.9 mu g mL(-1)). These simple chalcones have safe potential uses in antioxidant, antimicrobial and anti-inflammatory therapies.

  DOI：

  10.21577/0103-5053.20180177

文献信息

• Structure−Activity Relationship Studies of Chalcone Leading to 3-Hydroxy-4,3′,4′,5′-tetramethoxychalcone and Its Analogues as Potent Nuclear Factor κB Inhibitors and Their Anticancer Activities
  作者：Balasubramanian Srinivasan、Thomas E. Johnson、Rahul Lad、Chengguo Xing

  DOI：10.1021/jm901278z

  日期：2009.11.26

  Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-kappa B) activation. The structures of chalcone-based NF-kappa B inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-kappa B inhibition, to explore the feasibility of developing simple chalcone-based potent NF-kappa B inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-kappa B inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-kappa B inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-kappa B inhibitory activities, suggesting that suppressing NF-kappa B activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.