dihydrokaempferide | 3570-69-2

• 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: dihydrokaempferide
• 英文别名: 3,5,7-Trihydroxy-4'-methoxy-flavanon；Flavanone, 3,5,7-trihydroxy-4'-methoxy-；3,5,7-trihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 3570-69-2；137225-59-3
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: CKDYDMSDCNQHEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dihydrokaempferide 在 potassium pyrosulfite 作用下， 以 乙醇 为溶剂， 以55%的产率得到山奈素
  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 盐酸 、 双氧水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 dihydrokaempferide
  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

• Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
  作者：Chunling Hu、Zongbao Zhou、Yuanhang Xiang、Xiaoying Song、Hong Wang、Kaiqi Tao、Xiaochuan Ye

  DOI：10.1007/s00044-017-2054-z

  日期：2018.1

  Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and

  设计并合成了三十种二氢黄酮醇衍生物（D1 - D30），同时在光谱分析的基础上对合成的化合物进行了表征。它们对脂多糖（LPS）刺激的鼠RAW 264.7巨噬细胞中促炎性诱导白介素1β（IL-1β），白介素6（IL-6）和肿瘤坏死因子-α（TNF-α）的抑制活性为评估并显示出各种效率。化合物D1 - D30在20μM的浓度下对RAW 264.7细胞无毒作用；其中，化合物D9，D13和D19通过降低IL-1β，IL-6和TNF-α表现出最佳的抗炎活性。此外，初步讨论了它们的结构-活性关系。
• 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.
• GREENAWAY, W.;MAY, J.;WHATLEY, F. R., J. CHROMATOGR., 472,(1989) N, C. 393-400
  作者：GREENAWAY, W.、MAY, J.、WHATLEY, F. R.

  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。