3-(3,4-dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one | 1182706-74-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(3,4-dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one
• 英文别名: 3-(3,4-dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)chromen-4-one
• CAS: 1182706-74-6
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: CHRLFWDQCVNSPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one 、 3,4-二甲氧基苯乙胺 以 乙醇 为溶剂， 反应 3.0h， 以69%的产率得到7-{3-[(3,4-dimethoxyphenethyl)amino]-2-hydroxypropoxy}-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  发现 3-氨基-2-羟基丙氧基异黄酮衍生物作为潜在的抗 HCV 药物

  摘要：

  描述了某些 3-氨基-2-羟基-丙氧基异黄酮衍生物 6a-i 的合成和抗丙型肝炎病毒（抗 HCV）作用。已知的 3-(3,4-二甲氧基苯基)-7-(环氧乙烷-2-基甲氧基)-4H-chromen-4-one (5) 与取代的胺反应得到所需的异黄酮衍生物 6a-i。其中，7-{3-[(3,4-二甲氧基-苯乙基)氨基]-2-羟基丙氧基}-3-(3,4-二甲氧基苯基)-4H-chromen-4-one (6b)活性最强，表现出比标准抗病毒药物利巴韦林高约 2 倍的抗 HCV 效果（EC50 为 6.53 与 13.16 μM）。此外，化合物 6b 的细胞毒性低于利巴韦林。6b 的选择性指数 (SI) 比利巴韦林高约 2.6 倍。还发现化合物6e、6h和6i比利巴韦林具有更高的抗HCV作用。发现化合物6b以剂量依赖性方式抑制Ava5细胞中HCV RNA的表达；此外，我们发现化合物 6b、6e、6h

  DOI：

  10.3390/molecules23112863
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.0h， 生成 3-(3,4-dimethoxyphenyl)-7-(oxiran-2-ylmethoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthetic analogs of daidzein, having more potent osteoblast stimulating effect

  摘要：

  A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.008

文献信息

• New Aloperine–Isoflavone Conjugates
  作者：S. P. Bondarenko、M. S. Frasinyuk、V. P. Khilya

  DOI：10.1007/s10600-016-1723-3

  日期：2016.7

  The reaction of aloperine with isoflavone glycidyl ethers was investigated. A series of alkaloid–isoflavonoid conjugates were synthesized via regioselective opening of the oxirane ring by aloperine.

  研究了阿洛哌啶与异黄酮缩水甘油醚的反应。通过阿洛哌啶对环氧乙烷环的区域选择性打开，合成了一系列生物碱-异黄酮共轭物。
• ISOFLAVONE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：TZENG Cherng-Chyi

  公开号：US20090215767A1

  公开（公告）日：2009-08-27

  An isoflavone derivative is provided. The isoxazole derivative has following formula: wherein R 1 and R 2 , independently, include C 1 -C 12 alkyl optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy, and R 3 includes hydrogen, hydroxy or C 1 -C 12 alkoxy optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy. The invention also provides a pharmaceutical composition for treatment of osteoporosis including an isoflavone derivative or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

  提供了一种异黄酮衍生物。该异噁唑衍生物具有以下结构式：其中R1和R2独立地包括C1-C12烷基，可选择地取代为环氧丙烷、硫代环氧丙烷、环氮丙烷、氨基、环氨基、氨基羟基或环氨基羟基；R3包括氢、羟基或C1-C12烷氧基，可选择地取代为环氧丙烷、硫代环氧丙烷、环氮丙烷、氨基、环氨基、氨基羟基或环氨基羟基。该发明还提供了一种用于治疗骨质疏松症的药物组合物，包括一种异黄酮衍生物或其药用盐以及一种药学上可接受的载体。
• Synthesis of 7-(N-12-Cytisinylpropoxy)Isoflavones
  作者：S. P. Bondarenko、O. G. Makarenko、V. I. Vinogradova、M. S. Frasinyuk

  DOI：10.1007/s10600-020-03222-9

  日期：2020.11

  The reactions of cytisine with isoflavone glycidyl ethers were investigated. A series of cytisine–isoflavone conjugates were regioselectively synthesized via opening the oxirane ring by cytisine.

  研究了金雀花碱与异黄酮缩水甘油醚的反应。通过金雀花碱打开环氧乙烷环，区域选择性地合成了一系列金雀花碱-异黄酮缀合物。
• Isoflavone derivatives and pharmaceutical compositions comprising the same
  申请人：Kaosiung Medical University

  公开号：US07618998B2

  公开（公告）日：2009-11-17

  An isoflavone derivative is provided. The isoxazole derivative has following formula: wherein R1 and R2, independently, include C1-C12 alkyl optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy, and R3 includes hydrogen, hydroxy or C1-C12 alkoxy optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy. The invention also provides a pharmaceutical composition for treatment of osteoporosis including an isoflavone derivative or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

  提供一种异黄酮衍生物。该异噁唑衍生物具有以下式子：其中R1和R2，独立地，包括C1-C12烷基，可选地取代氧环丙烷、硫环丙烷、氮杂环丙烷、氨基、环氨基、氨基羟基或环氨基羟基；R3包括氢、羟基或C1-C12烷氧基，可选地取代氧环丙烷、硫环丙烷、氮杂环丙烷、氨基、环氨基、氨基羟基或环氨基羟基。本发明还提供了一种用于治疗骨质疏松症的药物组合物，包括一种异黄酮衍生物或其药学上可接受的盐和药学上可接受的载体。
• US7618998B2
  申请人：——

  公开号：US7618998B2

  公开（公告）日：2009-11-17