4-methoxy-2',4',6'-trimethoxymethoxychalcone

• 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: 4-methoxy-2',4',6'-trimethoxymethoxychalcone
• 英文别名: 3-(4-methoxyphenyl)-1-[2,4,6-tris(methoxymethoxy)phenyl]prop-2-en-1-one
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: DFOGIYAWUKESDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-methoxy-2',4',6'-trimethoxymethoxychalcone 在 盐酸 、 potassium pyrosulfite 、 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 4.33h， 生成 山奈素
  参考文献：
  名称：

  Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs

  摘要：

  A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.008
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-methoxy-2',4',6'-trimethoxymethoxychalcone
  参考文献：
  名称：

  二氢黄酮醇衍生物作为抗炎剂的合成，生物学评估和分子对接

  摘要：

  通过经典的阿尔加-弗林-奥马达（AFO）反应从查耳酮合成了一系列二氢黄酮醇衍生物（4a - 4l），并在光谱分析的基础上进行了表征。评估了所有合成的化合物对脂多糖（LPS）刺激的RAW 264.7细胞系中促炎性诱导的TNF-α，IL-1beta和IL-6的抑制活性，并显示了多种功效。此外，通过使用两个经典模型选择化合物4d和4k来检查其体内抗炎活性。此处化合物4k与阿司匹林和美洛昔康这两个参考文献相比，在小鼠耳部肿胀模型中显示出最大的抗炎活性，抑制率为32.98％，在大鼠爪水肿模型中，间隔2小时的抑制作用为40.06％。在较低剂量下观察到类似的效果。此外，将化合物4k与环氧合酶-2对接以验证获得的药理数据，并为观察到的抗炎活性提供可理解的证据。

  DOI：

  10.1007/s00044-019-02340-6

文献信息

• 二氢黄酮衍生物、其制备方法和用途
  申请人：首都医科大学宣武医院

  公开号：CN106977506B

  公开（公告）日：2020-04-24

  本发明涉及二氢黄酮衍生物、其制备方法和用途，具体涉及如式I所示化合物或其药学上可接受的盐、其药物组合物、其制备方法及其预防或治疗精神障碍和神经系统疾病的用途。本发明的化合物具有优秀的抑制小胶质细胞活化和神经炎症反应活性，并能拮抗多巴胺2型受体，改善多种精神障碍动物模型的行为学变化，而且还能有效抑制神经炎症和髓鞘脱失，可用于精神障碍和神经系统疾病的预防或治疗。
• Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship
  作者：Wen-Jun Jiang、Kan’ichiro Ishiuchi、Megumi Furukawa、Tomoko Takamiya、Susumu Kitanaka、Hiroshi Iijima

  DOI：10.1016/j.bmc.2015.09.042

  日期：2015.11

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.
• Hano. Yoshio; Mitsui, Pedro; Nomura, Taro, Heterocycles, 1990, vol. 30, # 2, p. 1023 - 1030
  作者：Hano. Yoshio、Mitsui, Pedro、Nomura, Taro

  DOI：——

  日期：——
• Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs
  作者：N. Pandurangan、Chinchu Bose、A. Banerji

  DOI：10.1016/j.bmcl.2011.07.008

  日期：2011.9

  A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis, biological evaluation, and molecular docking of dihydroflavonol derivatives as anti-inflammatory agents
  作者：Yuanhang Xiang、Chunling Hu、Yuejie Zhang、Xiaochuan Ye

  DOI：10.1007/s00044-019-02340-6

  日期：2019.6

  A series of dihydroflavonol derivatives (4a–4l) were synthesized from chalcones via classical Algar–Flynn–Oyamada (AFO) reaction and characterized on the basis of spectroscopic analyses. All synthesized compounds were evaluated for their inhibitory activity against the pro-inflammatory-inducible TNF-alpha, IL-1beta, and IL-6 in lipopolysaccharide (LPS)-stimulated RAW 264.7 cell lines and showed various

  通过经典的阿尔加-弗林-奥马达（AFO）反应从查耳酮合成了一系列二氢黄酮醇衍生物（4a - 4l），并在光谱分析的基础上进行了表征。评估了所有合成的化合物对脂多糖（LPS）刺激的RAW 264.7细胞系中促炎性诱导的TNF-α，IL-1beta和IL-6的抑制活性，并显示了多种功效。此外，通过使用两个经典模型选择化合物4d和4k来检查其体内抗炎活性。此处化合物4k与阿司匹林和美洛昔康这两个参考文献相比，在小鼠耳部肿胀模型中显示出最大的抗炎活性，抑制率为32.98％，在大鼠爪水肿模型中，间隔2小时的抑制作用为40.06％。在较低剂量下观察到类似的效果。此外，将化合物4k与环氧合酶-2对接以验证获得的药理数据，并为观察到的抗炎活性提供可理解的证据。