2’,4’-dihydroxyphenyl-5-methoxy-2H-chromen-3-ylmethanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 2’,4’-dihydroxyphenyl-5-methoxy-2H-chromen-3-ylmethanone
• 英文别名: 5-methoxybenzo-2H-pyran-3-yl-2′,3′-(dihydroxyphenyl)ketone；(2,4-dihydroxyphenyl)-(5-methoxy-2H-chromen-3-yl)methanone
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: VKZXSRABIPFNOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基-6-甲氧基苯甲醛 在 三乙烯二胺 、 manganese(IV) oxide 、 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.83h， 生成 2’,4’-dihydroxyphenyl-5-methoxy-2H-chromen-3-ylmethanone
  参考文献：
  名称：

  Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

  摘要：

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.037

文献信息

• 一种苯并吡喃类化合物、及其制备方法和药物组合物与用途
  申请人：中国医学科学院药物研究所

  公开号：CN110240583A

  公开（公告）日：2019-09-17

  本发明公开了如式Ⅰ所示的苯并吡喃类化合物，苯并吡喃类化合物的制备方法，含有这类化合物的组合物以及这类化合物在制备法尼酯X受体拮抗剂、肝脏保护剂、防治高血脂、防治2型糖尿病的药物中的用途。
• Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists
  作者：Guoning Zhang、Shuainan Liu、Wenjuan Tan、Ruchi Verma、Yuan Chen、Deyang Sun、Yi Huan、Qian Jiang、Xing Wang、Na Wang、Yang Xu、Chiwai Wong、Zhufang Shen、Ruitang Deng、Jinsong Liu、Yanqiao Zhang、Weishuo Fang

  DOI：10.1016/j.ejmech.2017.02.037

  日期：2017.3

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.