3-(4-hydroxyphenyl)-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one | 1449479-68-8

• 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-(4-hydroxyphenyl)-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one
• 英文别名: 7-O-propargyldaidzein；3-(4-Hydroxyphenyl)-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one；3-(4-hydroxyphenyl)-7-prop-2-ynoxychromen-4-one
• CAS: 1449479-68-8
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: PXHOIJUPKMBBRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  515.9±50.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-7-(prop-2-yn-1-yloxy)-4H-chromen-4-one 在 cesium fluoride 、 N,N-二乙基苯胺 作用下， 以34%的产率得到3-(4-hydroxyphenyl)-8-methyl-4H-furo[2,3-h]chromen-4-one
  参考文献：
  名称：

  [EN] ENHANCED OSTEOGENIC ACTIVITY OF DAIDZEIN ANALOGS ON HUMAN MESENCHYMAL STEM CELLS
  [FR] ACTIVITÉ OSTÉOGÉNIQUE ACCRUE D'ANALOGUES DE LA DAIDZÉINE SUR LES CELLULES SOUCHES MÉSENCHYMATEUSES HUMAINES

  摘要：

  公开号：

  WO2014165723A3
• 作为产物：
  描述：

  大豆甙元 、 3-溴丙炔 在 sodium hydride 作用下， 以 丙酮 、 甲苯 为溶剂， 以57%的产率得到3-(4-hydroxyphenyl)-7-(prop-2-yn-1-yloxy)-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

• An approach to C-glycosidic conjugates of isoflavones
  作者：Wiesław Szeja、Piotr Świerk、Grzegorz Grynkiewicz、Aleksandra Rusin、Katarzyna Papaj

  DOI：10.1515/hc-2013-0023

  日期：2013.4.1

  A novel approach to isoflavone glycoconjugates, designed as less biodegradable congeners of natural glycosides, is presented on example of daidzein linkage to a C-glycosidic synthon derived from l-rhamnose. 1,3-Dipolar cycloaddition was employed for chemical ligation of daidzein 7-O-propargyl ester and alkyl azide containing 2,3-unsaturated pyranoside moiety. The obtained constructs with opposite anomeric configuration both exhibited a considerable increase in cytotoxic activity against the HTC 116 cell line, in comparison to the parent isoflavone.

  摘要：提出了一种新的异黄酮糖苷结构方法，设计为天然糖苷的不易生物降解的同分异构体，以大豆黄酮与从l-鼠李糖衍生的C-糖苷合成物为例进行了研究。使用1,3-偶极环加成法将大豆黄酮7-O-丙炔酯和含有2,3-不饱和吡喃苷基的烷基叠氮化合物进行化学连接。所得构建物具有相反的异构构型，与母体异黄酮相比，对HTC 116细胞系的细胞毒活性均显著增加。
• 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。
• 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
• Design, Synthesis, and Osteogenic Activity of Daidzein Analogs on Human Mesenchymal Stem Cells
  作者：Amy L. Strong、Quan Jiang、Qiang Zhang、Shilong Zheng、Stephen M. Boue、Steven Elliott、Matthew E. Burow、Bruce A. Bunnell、Guangdi Wang

  DOI：10.1021/ml400397k

  日期：2014.2.13

  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.
• [EN] ENHANCED OSTEOGENIC ACTIVITY OF DAIDZEIN ANALOGS ON HUMAN MESENCHYMAL STEM CELLS<br/>[FR] ACTIVITÉ OSTÉOGÉNIQUE ACCRUE D'ANALOGUES DE LA DAIDZÉINE SUR LES CELLULES SOUCHES MÉSENCHYMATEUSES HUMAINES
  申请人：UNIV TULANE

  公开号：WO2014165723A3

  公开（公告）日：2014-12-31