2-(4-hydroxy-phenyl)-2,3-dihydro-benzo[h]chromen-4-one | 110973-41-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-hydroxy-phenyl)-2,3-dihydro-benzo[h]chromen-4-one
• 英文别名: 2-(4-Hydroxy-phenyl)-2,3-dihydro-benzo[h]chromen-4-on；2-(4-hydroxyphenyl)-2H-benzo[h]chromen-4(3H)-one；2-(4-hydroxyphenyl)-2,3-dihydrobenzo[h]chromen-4-one
• CAS: 110973-41-6
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: XVZQPMBTMVZZAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-phenyl)-2,3-dihydro-benzo[h]chromen-4-one 在 sodium tetrahydroborate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 2,4-trans-7,8-benzo-4'-hydroxy-flavan-4-ol 、 2,4-cis-7,8-benzo-4'-hydroxy-flavan-4-ol
  参考文献：
  名称：

  Lead optimization of 4-imidazolylflavans: New promising aromatase inhibitors

  摘要：

  Our previous studies have shown that several 7-substituted-4-imidazolylflavans are potent inhibitors of aromatase. These compounds were designed considering the anti-aromatase effect of some natural flavonoids and the importance of an azole ring for synthetic inhibitors such as letrozole or anastrozole towards binding to the heme iron of aromatase. In this study, we report the optimization of these lead compounds by the modulation of flavan A ring. The resulting 7,8-benzo-4-imidazolylflavans were tested in order to assess their ability to inhibit aromatase. Biological data concerning enantiomers obtained from the chiral separation of the racemate compound 4-imidazolyl-7-methoxyflavan are also presented. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.043
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 在 硫酸 、 barium(II) hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(4-hydroxy-phenyl)-2,3-dihydro-benzo[h]chromen-4-one
  参考文献：
  名称：

  Lead optimization of 4-imidazolylflavans: New promising aromatase inhibitors

  摘要：

  Our previous studies have shown that several 7-substituted-4-imidazolylflavans are potent inhibitors of aromatase. These compounds were designed considering the anti-aromatase effect of some natural flavonoids and the importance of an azole ring for synthetic inhibitors such as letrozole or anastrozole towards binding to the heme iron of aromatase. In this study, we report the optimization of these lead compounds by the modulation of flavan A ring. The resulting 7,8-benzo-4-imidazolylflavans were tested in order to assess their ability to inhibit aromatase. Biological data concerning enantiomers obtained from the chiral separation of the racemate compound 4-imidazolyl-7-methoxyflavan are also presented. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.043

文献信息

• New 7,8-benzoflavanones as potent aromatase inhibitors: Synthesis and biological evaluation
  作者：Samir Yahiaoui、Catherine Fagnere、Christelle Pouget、Jacques Buxeraud、Albert-José Chulia

  DOI：10.1016/j.bmc.2007.10.057

  日期：2008.2.1

  Some natural compounds such as flavonoids are known to possess a moderate inhibitory activity against aromatase, this enzyme being an interesting target for hormone-dependent breast cancer treatment. It has been demonstrated that the modulation of flavonoid skeleton could increase anti-aromatase effect. Therefore, new 7,8-benzoflavanones were synthesized and tested for their activity toward aromatase inhibition. It was observed that the introduction of a benzo ring at position C-7 and C-8 on flavanone skeleton led to new potent aromatase inhibitors, the resulting 7,8-benzoflavanones being until nine times more potent than amino-gluthetimide (the first aromatase inhibitor used clinically). (C) 2007 Elsevier Ltd. All rights reserved.
• Suzuki et al., Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., 1957, vol. <I> 41, p. 42,44
  作者：Suzuki et al.

  DOI：——

  日期：——
• Fujise et al., Nippon Kagaku Zasshi, 1956, vol. 77, p. 1833
  作者：Fujise et al.

  DOI：——

  日期：——
• Lead optimization of 4-imidazolylflavans: New promising aromatase inhibitors
  作者：Samir Yahiaoui、Christelle Pouget、Jacques Buxeraud、Albert José Chulia、Catherine Fagnère

  DOI：10.1016/j.ejmech.2011.03.043

  日期：2011.6

  Our previous studies have shown that several 7-substituted-4-imidazolylflavans are potent inhibitors of aromatase. These compounds were designed considering the anti-aromatase effect of some natural flavonoids and the importance of an azole ring for synthetic inhibitors such as letrozole or anastrozole towards binding to the heme iron of aromatase. In this study, we report the optimization of these lead compounds by the modulation of flavan A ring. The resulting 7,8-benzo-4-imidazolylflavans were tested in order to assess their ability to inhibit aromatase. Biological data concerning enantiomers obtained from the chiral separation of the racemate compound 4-imidazolyl-7-methoxyflavan are also presented. (C) 2011 Elsevier Masson SAS. All rights reserved.