2’,4’-dimethoxy-6’-hydroxy-4-O-methoxymethylchalcone | 77184-69-1

• 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: 2’,4’-dimethoxy-6’-hydroxy-4-O-methoxymethylchalcone
• 英文别名: 2'-Hydroxy-4',6'-dimethoxy-4-(methoxymethoxy)chalcone；1-(2-hydroxy-4,6-dimethoxyphenyl)-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 77184-69-1
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: KCJFDDQHNVOPBL-UHFFFAOYSA-N

物化性质

• 沸点：
  548.7±50.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2’,4’-dimethoxy-6’-hydroxy-4-O-methoxymethylchalcone 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 flavokawain C
  参考文献：
  名称：

  In Vitro Osteogenic Differentiation and Antibacterial Potentials of Chalcone Derivatives

  摘要：

  Chalcone derivatives have been investigated as therapeutic agents for the anticancer, antioxidant, and anti-inflammatory fields. In this study, we have synthesized four different types of chalcone derivatives and demonstrated in vitro bioactivities. We divided these derivatives into two groups of chalcones on the basis of similar substituents on the aromatic rings, and we tested cell viability and proliferation potentials, which indicated that the methoxy substituent on the A ring could enhance cytotoxicity and antiproliferation potential depending on the chalcone concentration. We also investigated osteogenic differentiation of C2C12 cells by ALP staining, the early marker for osteogenesis, which demonstrated that the chalcones could not only induce activity of BMP-2 but also inhibit the activity of noggin, a BMP antagonist. In addition, chalcone bearing hydroxyl groups at the 2-, 4-, and 6-position on the A ring inhibited treptococcus mutans growth, a major causative agent of dental caries. Therefore, we concluded that the chalcone derivatives synthesized in this research can be good candidates for therapeutic agents promoting bone differentiation, with an expectation of inhibiting S. mutans, in dentistry.

  DOI：

  10.1021/acs.molpharmaceut.8b00288
• 作为产物：
  描述：

  间苯三酚 在 盐酸 、 potassium carbonate 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 55.5h， 生成 2’,4’-dimethoxy-6’-hydroxy-4-O-methoxymethylchalcone
  参考文献：
  名称：

  异甘草黄酮醇的合成方法

  摘要：

  本发明提供一种异甘草黄酮醇的合成方法，包括：将2,4‑O‑保护基R1‑6‑羟基‑苯乙酮与4‑O‑保护基R2‑苯甲醛进行缩合，生成2’,4’‑O‑保护基R1‑6’‑羟基‑4‑O‑保护基R2‑查耳酮；将上述查耳酮氧化生成黄酮醇；将黄酮醇的3‑OH进行选择保护，得到3,5,7‑O‑保护基R1‑4’‑O‑保护基R2‑黄酮醇；将3,5,7‑O‑保护基R1‑4’‑O‑保护基R2‑黄酮醇脱除保护基R2，得到3,5,7‑O‑保护基R1‑4’‑羟基‑黄酮醇；4’‑OH位进行1,1‑二甲基炔丙基化，得到3,5,7‑O‑保护基R1‑4’‑O‑(1”,1”‑二甲基丙炔基)黄酮醇；在催化剂作用下使所述3,5,7‑O‑保护基R1‑4’‑O‑(1”,1”‑二甲基丙炔基)黄酮醇的炔基部分加氢，得3,5,7‑O‑保护基R1‑4’‑O‑(1”,1”‑二甲基丙烯基)黄酮醇；将3,5,7‑O‑保护基R1‑4’‑O‑(1”,1”‑二甲基丙烯基)黄酮醇进行克莱森重排，得到3,5,7‑O‑保护基异R1‑甘草黄酮醇；将3,5,7‑O‑保护基异R1‑甘草黄酮醇脱除保护基R1，得到所述异甘草黄酮醇。

  公开号：

  CN112047916A

文献信息

• Phosphonooxy- or glycosyloxy-substituted acrylophenones, compositions
  申请人：Hoffmann-La Roche Inc.

  公开号：US04327088A1

  公开（公告）日：1982-04-27

  Compounds of the formula: ##STR1## wherein R.sub.1 is hydroxy, phosphonooxy, aminoglycosyloxy, acylaminoglycosyloxy, benzyloxycarbonyloxy, arylcarbonyloxy, trialkylammonio-acyloxy or furoyloxy; R.sub.2 and R.sub.3 each are lower alkoxy; and R.sub.4 is benzimidazolyl, furyl which is unsubstituted or substituted with lower alkyl, thienyl which is unsubstituted or substituted with lower alkyl, or phenyl which is substituted with lower alkyl, lower alkoxy, alkoxyalkoxy, alkylthio, alkylenedioxy, or acyloxy, with the proviso that when R.sub.1 is hydroxy, R.sub.4 is benzimidazolyl or phenyl which is substituted by acyloxy or alkoxyalkoxy, or pharmaceutically acceptable salts thereof useful as antiviral agents.

  式为：##STR1##的化合物，其中R.sub.1为羟基、磷酸酯氧基、氨基糖苷氧基、酰基氨基糖苷氧基、苄氧羰基氧基、芳基羰基氧基、三烷基铵基酰氧基或呋喃氧基；R.sub.2和R.sub.3各自为低烷氧基；R.sub.4为苯并咪唑基、未取代或取代有低烷基的呋喃基、未取代或取代有低烷基的噻吩基，或取代有低烷基、低烷氧基、烷氧烷氧基、烷基硫氧基、烷基二氧基或酰氧基的苯基，但当R.sub.1为羟基时，R.sub.4为苯并咪唑基或取代有酰氧基或烷氧烷氧基的苯基，或其药学上可接受的盐，用作抗病毒剂。
• Synthesis, Cytotoxicity, and Antioxidative Activity of Minor Prenylated Chalcones from <i>Humulus lupulus</i>
  作者：Susanne Vogel、Jörg Heilmann

  DOI：10.1021/np800188b

  日期：2008.7.1

  The minor hop (Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1 '',2 ''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconar-. ingenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC50 values comparable to xanthohumol (8.2-19.2 mu M). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.