7-(2-(dimethylamino)ethoxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one | 38588-59-9

• 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: 7-(2-(dimethylamino)ethoxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 7-(2-Dimethylaminoethoxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one；7-[2-(Dimethylamino)ethoxy]-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 38588-59-9
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: FGDAXVSWOUJWBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  大豆甙元 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以61%的产率得到7-(2-(dimethylamino)ethoxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Design, Synthesis, and Osteogenic Activity of Daidzein Analogs on Human Mesenchymal Stem Cells

  摘要：

  Osteoporosis is caused by an overstimulation of osteoclast activity and the destruction of the bone extracellular matrix. Without the normal architecture, osteoblast cells are unable to rebuild phenotypically normal bone. Hormone replacement therapy with estrogen has been effective in increasing osteoblast activity but also has resulted in the increased incidence of breast and uterine cancer. In this study we designed and synthesized a series of daidzein analogs to investigate their osteogenic induction potentials. Human bone marrow derived mesenchymal stem cells (MSCs) from three different donors were treated with daidzein analogs and demonstrated enhanced osteogenesis when compared to daidzein treatment. The enhanced osteogenic potential of these daidzein analogs resulted in increased osterix (Sp7), alkaline phosphatase (ALP), osteopontin (OPN), and insulin-like growth factor 1 (IGF-1), which are osteogenic transcription factors that regulate the maturation of osteogenic progenitor cells into mature osteoblast cells.

  DOI：

  10.1021/ml400397k

文献信息

• Enhanced Osteogenic Activity of Daidzein Analogs on Human Mesenchymal Stem Cells
  申请人：THE ADMINISTRATORS OF THE TULANE EDUCATIONAL FUND

  公开号：US20160068542A1

  公开（公告）日：2016-03-10

  Disclosed are daidzein analogs having the formula (I). Also disclosed are compositions, include a disclosed daidzein analogs, methods of preventing or treating bone disease or bone injury and/or stimulating bone growth, in a subject that include administering to the subject an effective amount of disclosed daidzein analog. Disclosed are isolated mesenchymal stem cell that has been altered by treatment a disclosed daidzein analog, daidzein, glycinol, glyceollin I, or glyceollin II, to increase the osteogenic potential of the mesenchymal stem cells.

  本发明揭示了具有公式（I）的daidzein类似物。还揭示了包括所述daidzein类似物的组合物，用于预防或治疗骨疾病或骨损伤和/或刺激骨生长的方法，包括向受体施用揭示的daidzein类似物的有效量。本发明揭示了已通过处理揭示的daidzein类似物，daidzein，glycinol，glyceollin I或glyceollin II而改变的分离的间充质干细胞，以增加间充质干细胞的成骨潜能。
• Design, synthesis and the evaluation of cholinesterase inhibition and blood‐brain permeability of daidzein derivatives or analogs
  作者：Yi‐Hui Wang、Xiao‐Hui Gao、Xuan Li、Yu‐Jie Ding、Qing Shi、Zhi‐Yu Yang、Dian Peng、Hao‐Ran Liu

  DOI：10.1111/cbdd.14279

  日期：2023.10

  In the present study, a series of derivatives and analogs of daidzein were designed and synthesized to investigate cholinesterase inhibition and blood–brain barrier permeability. The enzyme assay showed that most of the compounds containing a tertiary amine group exhibit moderate cholinesterase inhibition, 7-hydroxychromone derivatives (absence of B ring of daidzein scaffold) only have a weaker bioactivity

  在本研究中，设计并合成了一系列大豆黄酮衍生物和类似物，以研究胆碱酯酶抑制和血脑屏障通透性。酶测定结果表明，大多数含有叔胺基团的化合物具有中等程度的胆碱酯酶抑制作用，7-羟基色酮衍生物（黄豆苷元支架中不含B环）仅具有较弱的生物活性，而那些不含叔胺基团的化合物则没有生物活性。其中化合物15a（4'- N,N-二甲基氨基乙氧基-7-甲氧基异黄酮）表现出最好的抑制活性（IC 50：2.14±0.31μmol/L），并且对AChE的选择性高于BuChE（比率：7.07）。选择它通过 UPLC-MS/MS 进行进一步研究。结果显示，化合物15a在小鼠体内的C脑/血清在240分钟内大于2.87。这一发现可能为未来中枢神经药物（包括但不限于胆碱酯酶抑制剂）的开发提供有价值的信息。
• Ground mixture
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0129893A2

  公开（公告）日：1985-01-02

  A ground mixture of a poorly soluble cystalline drug and an adsorbent is remarkably improved in the rates of dissolution and absorption of the drug.

  将溶解性较差的胱氨酸药物和吸附剂混合研磨后，可显著提高药物的溶解和吸收率。
• ENHANCED OSTEOGENIC ACTIVITY OF DAIDZEIN ANALOGS ON HUMAN MESENCHYMAL STEM CELLS
  申请人：The Administrators of the Tulane Educational Fund

  公开号：EP2981530A2

  公开（公告）日：2016-02-10
• US4772627A
  申请人：——

  公开号：US4772627A

  公开（公告）日：1988-09-20