2',4'-dimethoxyflavanone | 98583-84-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2',4'-dimethoxyflavanone
• 英文别名: 2-(2,4-dimethoxyphenyl)-2,3-dihydro-4H-chromen-4-one；2-(2,4-dimethoxy-phenyl)-chroman-4-one；2-(2,4-Dimethoxy-phenyl)-chroman-4-on；2-(2,4-dimethoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 98583-84-7
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: WLSKGTPEURXKTK-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  447.0±45.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',4'-dimethoxyflavanone 在 五氯化磷 、 苯 作用下， 生成 2,4-二甲氧基黄酮
  参考文献：
  名称：

  Hattori, Acta Phytochimica, 1932, vol. 6, p. 131,152

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二甲氧基苯甲醛 以 乙酸乙酯 为溶剂， 反应 10.0h， 生成 2',4'-dimethoxyflavanone
  参考文献：
  名称：

  Matsushima, Ryoka; Kageyama, Hiroyuki, Journal of the Chemical Society. Perkin transactions II, 1985, p. 743 - 748

  摘要：

  DOI：

文献信息

• Glycolytic Inhibition and Antidiabetic Activity on Synthesized Flavanone Scaffolds with Computer Aided Drug Designing Tools
  作者：Natarajan Kiruthiga、Govindaraj Saravanan、Chellappa Selvinthanuja、Kulandaivel Srinivasan、Thangavel Sivakumar

  DOI：10.2174/1570180817999201209204523

  日期：2021.8.10

  Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs available in the market in long-term use may lead to serious adverse effects. Hence, current research focuses on drug development for the management of diabetes by synthesizing natural mimicking flavonoid analogues.

  This study focused on the synthesis of flavanone derivatives imitating natural flavonoid core and investigated for their antidiabetic and antioxidant activity, which can help in the development of drug discovery targeting diabetic management.

  The novel 2-phenyl-2,3-dihydro-chromen-4-ones were synthesized from 1,3-diphenyl-prop-2-en-1-one derivatives and characterized using UV, IR, ¹HNMR, ¹³CNMR and mass spectroscopic techniques. Drug target site was determined using graph theoretical analysis and screened the characterized title compounds for their in-silico studies by analyzing their physiochemical properties, ADMET studies, and molecular docking analysis. Antidiabetic and free radical scavenging effects were investigated both by in-vitro (alpha-amylase inhibitory assay) and in-vivo models. Streptozotocin (STZ) induced rats were used as in-vivo models.

  The α-amylase inhibitory assay showed flavanones with hydroxyl substitution HFA1- HFA7 had significant IC50 values. The test compounds (HFA3-HFA7) were investigated for their antidiabetic activity on STZ induced rats at 40 mg/kg. The blood glucose level and antioxidant enzymes were significantly restored by title compounds (HFA5, HFA4, and HFA6) with an electron-donating group such as hydroxyl, methoxy and thiophenyl group on ring B compared to glibenclamide.

  These results suggest that naturally mimicking synthesized flavanone have antidiabetic and antioxidant properties, which can aid in the development of drugs towards diabetes management.

  背景：糖尿病是一种具有挑战性的代谢紊乱，当HbA1c水平未得到控制时会导致一系列并发症。市场上现有的大部分长期使用的药物可能会导致严重的不良反应。因此，当前的研究重点在于通过合成天然模拟类黄酮类似物来开发治疗糖尿病的药物。 目标：本研究侧重于合成模拟天然类黄酮核心的黄酮衍生物，并对其抗糖尿病和抗氧化活性进行研究，这有助于开发针对糖尿病管理的药物发现。 材料和方法：从1,3-二苯基-丙-2-烯-1-酮衍生物合成了新型的2-苯基-2,3-二氢-香豆素，并利用紫外线、红外线、核磁共振、质谱等技术对其进行表征。通过图论分析确定了药物靶点位点，并通过对其物理化学性质、ADMET研究和分子对接分析进行了体外研究。通过体外（α-淀粉酶抑制实验）和体内模型研究了抗糖尿病和自由基清除效果。利用链脲霉素（STZ）诱导的大鼠作为体内模型。 结果：α-淀粉酶抑制实验显示，具有羟基取代的黄酮类物质HFA1-HFA7具有显著的IC50值。将试验化合物（HFA3-HFA7）以40 mg/kg剂量用于STZ诱导的大鼠，发现HFA5、HFA4和HFA6等具有电子给予基团（如羟基、甲氧基和硫苯基）的化合物明显恢复了血糖水平和抗氧化酶活性，与格列本脲相比。 结论：这些结果表明，天然模拟合成的黄酮类物质具有抗糖尿病和抗氧化性能，有助于开发针对糖尿病管理的药物。
• Gallagher et al., Journal of the Chemical Society, 1953, p. 3770,3777
  作者：Gallagher et al.

  DOI：——

  日期：——
• Shareef, Omar A.; Said, Said A.; Abdulrazaq, Ali Y., Journal of the Chemical Society of Pakistan, 2019, vol. 41, # 6, p. 1046 - 1054
  作者：Shareef, Omar A.、Said, Said A.、Abdulrazaq, Ali Y.

  DOI：——

  日期：——
• Aspergillus niger catalyzes the synthesis of flavonoids from chalcones
  作者：Julio Alarcón、Joel Alderete、Carlos Escobar、Ramiro Araya、Carlos L. Cespedes

  DOI：10.3109/10242422.2013.813489

  日期：2013.8

  Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus niger is capable of cyclizing chalcones to flavanones, affording a mimic of plant biosynthetic processes. Chalcones 1-6 were biotransformated to the modified chalcones 8-14 and to the flavanones 15-27. The biotransformation showed that enzymatic cyclization and demethylation occurred during the first days of biotransformation; in contrast, hydroxylation is a later process. With a longer culturing time, it is possible to obtain more hydroxylated flavanones with excellent yields.
• Imafuku, Kimiaki; Honda, Masaaki; McOmie, J. F. W., Synthesis, 1987, # 2, p. 199 - 201
  作者：Imafuku, Kimiaki、Honda, Masaaki、McOmie, J. F. W.

  DOI：——

  日期：——