3-(4-hydroxyphenyl)-7-isopropoxy-4H-chromen-4-one | 97846-18-9

• 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: 3-(4-hydroxyphenyl)-7-isopropoxy-4H-chromen-4-one
• 英文别名: 3-(4-hydroxyphenyl)-7-isopropoxychromen-4-one；4'-hydroxyipriflavone；7-Isopropoxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one；4H-1-Benzopyran-4-one, 3-(4-hydroxyphenyl)-7-(1-methylethoxy)-；3-(4-hydroxyphenyl)-7-propan-2-yloxychromen-4-one
• CAS: 97846-18-9
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: DEQMUPGWSXUDKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

4H-1-苯并吡喃-4-酮, 3-(4-羟基苯基)-7-(1-甲基乙氧基)-是伊普瑞氟韦已知的人体代谢物。

4H-1-Benzopyran-4-one, 3-(4-hydroxyphenyl)-7-(1-methylethoxy)- is a known human metabolite of ipriflavone.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-7-isopropoxy-4H-chromen-4-one 在 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 7-(1-methylethoxy)-3-{4-[4-(piperidin-1-yl)butoxy]phenyl}-4H-1-benzopyran-4-one hydrochloride
  参考文献：
  名称：

  Novel Basic Isoflavones as Inhibitors of Bone Resorption

  摘要：

  A number of aminoalkoxy analogues of ipriflavone (=7-(1-methylethoxy)isoflavone) were prepared and examined for their capacity to inhibit bone resorption induced by bovine parathyroid hormone fragment 1 - 34. Good-to-high activities were found for 7-(aminoalkoxy)isoflavone. analogues. Their activity was influenced by a number of structural features, among which the length of the basic side chain, the basicity of the amino group, and the nature and position of substituents on the 3-phenyl ring. 4'-(Aminoalkoxy)ipriflavone derivatives were less active.

  DOI：

  10.1002/1522-2675(20010815)84:8<2417::aid-hlca2417>3.0.co;2-n
• 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， 生成 3-(4-hydroxyphenyl)-7-isopropoxy-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

• Characterization of cytochrome P450s mediating ipriflavone metabolism in human liver microsomes
  作者：Y. Moon、S. Y. Kim、H. Y. Ji、Y. K. Kim、H.-J. Chae、S.-W. Chae、H. S. Lee

  DOI：10.1080/00498250601146962

  日期：2007.3

  seven metabolites (M1-M7). This study was performed to characterize the human liver cytochrome P450s (CYP) responsible for the metabolism of ipriflavone. Hydroxylation at the beta-ring to M3, O-dealkylation to M1 and oxidation at isopropyl group to M4 and M5 are major pathways for ipriflavone metabolism in three different human liver microsome preparations. The specific CYPs responsible for ipriflavone

  据报道，用于预防和治疗骨质疏松症的合成类黄酮伊普黄酮在人体中广泛代谢为7种代谢物（M1-M7）。进行这项研究的目的是鉴定负责依普黄酮代谢的人肝细胞色素P450（CYP）。在三种不同的人肝微粒体制剂中，乙炔异黄酮代谢的主要途径是在β环上羟基化成M3，在O上脱烷基化成M1和在异丙基上氧化成M4和M5。通过相关分析，免疫抑制，人肝微粒体的化学抑制以及表达的重组CYP酶的代谢相结合，鉴定了负责将依普黄酮氧化为活性代谢物M1，M3，M4和M5的特定CYP。依普黄酮及其五种代谢产物的抑制能力 在人肝微粒体中研究了7种具有临床意义的重要CYP的M1-M5。我们的研究结果表明，CYP3A4在伊普黄酮到M1的O-脱烷基作用中起主要作用，而CYP1A2在M3，M4和M5的形成中起主要作用。发现异黄酮和/或其五种代谢产物有效抑制CYP 1A2、2C8、2C9和2C19底物的代谢。
• 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。
• 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。
• Isoflavone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0136569A2

  公开（公告）日：1985-04-10

  Novel isoflavone derivatives of the formula: exhibit mild estrogenic activity, and are of value as an agent for prevention and treatment of osteoporosis.

  式中的新型异黄酮衍生物： 表现出温和的雌激素活性，具有预防和治疗骨质疏松症的价值。
• ISOFLAVONE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：CHIESI FARMACEUTICI S.p.A.

  公开号：EP0954520B1

  公开（公告）日：2002-04-10