5-ethoxyflavone | 162787-72-6

• 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: 5-ethoxyflavone
• 英文别名: 5-ethoxy-2-phenyl-4H-chromen-4-one；5-Ethoxy flavone；5-ethoxy-2-phenylchromen-4-one
• CAS: 162787-72-6
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: ARLSAHPUWKBRBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-dihydroxyacetophenone 在 硫酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 5-ethoxyflavone
  参考文献：
  名称：

  一种黄酮类化合物及其制备方法和用途

  摘要：

  本发明公开了一种黄酮类化合物及其制备方法和用途，其中黄酮类化合物包括黄酮类化合物FLM_1‑24、黄酮衍生物FLM_25‑40和异黄酮衍生物FLM_41‑48。本发明黄酮类化合物可用于制备对人肝癌细胞系Huh7细胞的Nogo‑B表达具有调节作用的调节剂，具体地说，本发明黄酮类化合物对人肝癌细胞系Huh7细胞的Nogo‑B表达具有良好的抑制活性。

  公开号：

  CN113512018B

文献信息

• Synthesis and Biological Evaluation of Substituted Flavones as Gastroprotective Agents
  作者：Jeffrey J. Ares、Pamela E. Outt、Jared L. Randall、Peter D. Murray、Pamela S. Weisshaar、Linda M. O'Brien、Beth L. Ems、Sunil V. Kakodkar、Gary R. Kelm

  DOI：10.1021/jm00025a011

  日期：1995.12

  Flavone (1) was found to protect against ethanol-induced gastric damage in rats; however, it is known that certain compounds in the flavone class, including flavone itself, are inducers of hepatic drug metabolizing enzymes. With the hope of identifying gastroprotective flavones that have minimal effects on drug metabolizing enzymes, we have synthesized and evaluated selected flavone analogs. Gastroprotective potency in the ethanol model was retained by methoxy substitution in the 5-position (4) and by methoxy (12) or methyl (14) substitution in the 7-position. A number of substituted analogs of the potent molecule 5-methoxyflavone (4) were also synthesized, and in many cases, these substitutions provided gastroprotective molecules. In order to assess liver enzyme induction potential, two of the gastroprotective flavones, 7-methoxyflavone (12) and 5-methoxy-4'-fluoroflavone (26), were examined for their effect on liver microsomal cytochrome P450 and 7-ethoxyresorufin O-dealkylase (CYP1A) activity. These two compounds caused minimal changes in the cytochrome P450 concentration and were considerably less potent than beta-naphthoflavone as inducers of CYP1A enzyme activity. Furthermore, following oral administration to rats, 5-methoxy-4'-fluoroflavone (26) was found to protect against indomethacin-induced gastric damage. These results indicate that, through appropriate substitution, flavones can be obtained that are gastroprotective but have minimal effects on drug-metabolizing enzymes.
• US5399584A
  申请人：——

  公开号：US5399584A

  公开（公告）日：1995-03-21
• 一种黄酮类化合物及其制备方法和用途
  申请人：合肥工业大学

  公开号：CN113512018B

  公开（公告）日：2023-07-18

  本发明公开了一种黄酮类化合物及其制备方法和用途，其中黄酮类化合物包括黄酮类化合物FLM_1‑24、黄酮衍生物FLM_25‑40和异黄酮衍生物FLM_41‑48。本发明黄酮类化合物可用于制备对人肝癌细胞系Huh7细胞的Nogo‑B表达具有调节作用的调节剂，具体地说，本发明黄酮类化合物对人肝癌细胞系Huh7细胞的Nogo‑B表达具有良好的抑制活性。