7-(2-bromo-ethoxy)-3-(4-hydroxy-phenyl)-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-(2-bromo-ethoxy)-3-(4-hydroxy-phenyl)-4H-chromen-4-one
• 英文别名: 7-O-(2-bromoethyl)-daidzein；7-(2-Bromoethoxy)-3-(4-hydroxyphenyl)chromen-4-one
• 化学式: C₁₇H₁₃BrO₄
• 分子量: 361.192
• InChiKey: XQTGVIFUPAUXIM-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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  7-(2-bromo-ethoxy)-3-(4-hydroxy-phenyl)-4H-chromen-4-one 、 三乙胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 7-O-(2-triethylaminoethyl)-daidzein bromide
  参考文献：
  名称：

  Daidzin derivatives for the treatment of alcohol dependence or alcohol abuse

  摘要：

  揭示了一种利用二氧化和类似于二氧化的化合物治疗酒精滥用的方法。还公开了一种筛选具有抗酒精依赖活性的化合物的方法。

  公开号：

  EP1645272A3
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-(4-羟基苯基)-乙酮 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 7-(2-bromo-ethoxy)-3-(4-hydroxy-phenyl)-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

• METHODS AND ASSAYS USEFUL IN THE TREATMENT OF ALCOHOL DEPENDENCE OR ALCOHOL ABUSE
  申请人：THE ENDOWMENT FOR RESEARCH IN HUMAN BIOLOGY, INC.

  公开号：EP1077697A1

  公开（公告）日：2001-02-28
• US6121010A
  申请人：——

  公开号：US6121010A

  公开（公告）日：2000-09-19
• [EN] METHODS AND ASSAYS USEFUL IN THE TREATMENT OF ALCOHOL DEPENDENCE OR ALCOHOL ABUSE<br/>[FR] PROCEDES ET METHODES DE CRIBLAGE UTILES POUR TRAITER LA DEPENDANCE A L'ALCOOL OU L'ABUS D'ALCOOL
  申请人：THE ENDOWMENT FOR RESEARCH IN HUMAN BIOLOGY, INC.

  公开号：WO1999058124A1

  公开（公告）日：1999-11-18

  (EN) A method for the treatment of alcohol abuse using diadzin and compounds analogous to diadzin is disclosed. Also disclosed is a method for screening compounds having antidipsotropic activity.(FR) L'invention concerne un procédé servant à traiter l'abus d'alcool au moyen de daidzine et de composés analogues à daidzine. Elle concerne également une méthode de criblage de composés exerçant une activité antidipsotropique.
• Synthetic analogs of daidzein, having more potent osteoblast stimulating effect
  作者：Dinesh K. Yadav、Abnish K. Gautam、Jyoti Kureel、Kamini Srivastava、Mahendra Sahai、Divya Singh、Naibedya Chattopadhyay、Rakesh Maurya

  DOI：10.1016/j.bmcl.2010.12.008

  日期：2011.1

  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.
• Daidzin derivatives for the treatment of alcohol dependence or alcohol abuse
  申请人：THE ENDOWMENT FOR RESEARCH IN HUMAN BIOLOGY, INC.

  公开号：EP1645272A3

  公开（公告）日：2008-11-05

  A method for the treatment of alcohol abuse using diadzin and compounds analogous to diadszin is disclosed. Also disclosed is a method for screening compounds having antidipsotropic activity.

  揭示了一种利用二氧化和类似于二氧化的化合物治疗酒精滥用的方法。还公开了一种筛选具有抗酒精依赖活性的化合物的方法。