7-hexyloxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

• 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-hexyloxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 7-hexyloxy-3-(4-hydroxyphenyl)chromen-4-one；7-hexoxy-3-(4-hydroxyphenyl)chromen-4-one
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: UDDYOFMACJTBDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴己烷 、 大豆甙元 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以40%的产率得到7-hexyloxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Effects of 7-O Substitutions on Estrogenic and Anti-Estrogenic Activities of Daidzein Analogues in MCF-7 Breast Cancer Cells

  摘要：

  Daidzein (1) is a natural estrogenic isoflavone. We report here that 1 can be transformed into anti-estrogenic ligands by simple alkyl substitutions of the 7-hydroxyl hydrogen. To test the effect of such structural modifications on the hormonal activities of the resulting compounds, a series of daidzein analogues have been designed and synthesized. When MCF-7 cells were treated with the analogues, those resulting from hydrogen substitution by isopropyl (3d), isobutyl (3f), cyclopentyl (3g), and pyrano- (2) inhibited cell proliferation, estrogen-induced transcriptional activity, and estrogen receptor (ER) regulated progesterone receptor (PgR) gene expression. However, methyl (3a) and ethyl (3b) substitutions of the hydroxyl proton only led to moderate reduction of the estrogenic activities. These results demonstrated the structural requirements for the transformation of daidzein from an ER agonist to an antagonist. The most effective analogue, 2, was found to reduce in vivo estrogen stimulated MCF-7 cell tumorigenesis using a xenograft mouse model.

  DOI：

  10.1021/jm100610w

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 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.
• Synthesis of Potential Antidipsotropic Isoflavones:  Inhibitors of the Mitochondrial Monoamine Oxidase−Aldehyde Dehydrogenase Pathway
  作者：Guang-Yao Gao、Dian-Jun Li、Wing Ming Keung

  DOI：10.1021/jm0101390

  日期：2001.9.1

  Recently we have shown that daidzin, the major active principle of an ancient herbal treatment for "alcohol addiction", suppresses ethanol intake in alcohol-preferring laboratory animals. Further, we have identified the monoamine oxidase (MAO)-aldehyde dehydrogenase (ALDH-2) pathway of the mitochondria as the potential site of action of daidzin. Daidzin analogues that potently inhibit ALDH-2 but have no or little effect on MAO are most antidipsotropic, whereas those that also inhibit MAO exhibit little, if any, antidipsotropic activity. Therefore, in the design and synthesis of more potent antidipsotropic analogues, structural features important for the inhibition of both ALDH-2 and MAO must be taken into consideration. To gain further information on the structure-activity relationships at the inhibitor binding sites of ALDH-2 and MAO, we prepared 44 analogues of daidzin and determined their potencies for ALDH-2 and MAO inhibition. Results indicate that a sufficient set of criteria for a potent antidipsotropic analogue is an isoflavone with a free 4 ' -OH function and a straight-chain alkyl substituent at the 7 position that has a terminal polar function such as -OH, -COOH, or -NH2. The preferable chain lengths for the 7-O-omega -hydroxy, 7-O-omega -carboxy, and 7-O-omega -amino subsitutents are 2 less than or equal to n less than or equal to 6, 5 less than or equal to 5 n less than or equal to 10, and n greater than or equal to 4, respectively. Analogues that meet these criteria have increased potency for ALDH-2 inhibition and/or decreased potency for MAO inhibition and therefore are likely to be potent antidipsotropic agents.
• 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
• NOVEL DAIDZEIN ANALOGS AS TREATMENT FOR CANCER
  申请人：Wang Guangdi

  公开号：US20130184475A1

  公开（公告）日：2013-07-18

  Provided are compositions for treatment of cancers, including breast cancer, comprising at least one novel daidzein analog, as well as methods of using the same for preventing or treating cancer or tumor growth.