7-ethoxyflavone | 93321-62-1

• 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: 7-ethoxyflavone
• 英文别名: 7-ethoxy-2-phenyl-4H-chromen-4-one；7-Ethoxy-flavon；7-ethoxy-2-phenyl-chromen-4-one；7-Aethoxy-2-phenyl-chromen-4-on；7-Ethoxy-2-phenylchromen-4-one
• CAS: 93321-62-1
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: KEPIEKIQUNUTHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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

• 作为反应物：
  描述：

  7-ethoxyflavone 、 sodium ethanolate 生成 4-乙氧基-2-羟基苯乙酮 、 苯甲酸
  参考文献：
  名称：

  Emilewicz; v. Kostanecki, Chemische Berichte, 1898, vol. 31, p. 704

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 7-ethoxyflavone
  参考文献：
  名称：

  Emilewicz; v. Kostanecki, Chemische Berichte, 1898, vol. 31, p. 704

  摘要：

  DOI：

文献信息

• Pyrrolidine and iodine catalyzed domino aldol-Michael-dehydrogenative synthesis of flavones
  作者：Mayuri M. Naik、Santosh G. Tilve、Vijayendra P. Kamat

  DOI：10.1016/j.tetlet.2014.04.051

  日期：2014.5

  A one pot synthesis of flavones is established from 2′-hydroxyacetophenones and substituted aromatic aldehydes. The method uses domino aldol-Michael-oxidation reaction catalyzed by pyrrolidine as a base and iodine as an oxidant in dimethyl sulfoxide.

  由2'-羟基苯乙酮和取代的芳族醛建立黄酮的一锅合成法。该方法以吡咯烷为碱，碘为氧化剂，在二甲基亚砜中催化多米诺羟醛-迈克尔-氧化反应。
• 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
• v. Kostanecki; Rozycki, Chemische Berichte, 1901, vol. 34, p. 3726
  作者：v. Kostanecki、Rozycki

  DOI：——

  日期：——
• Emilewicz; v. Kostanecki, Chemische Berichte, 1898, vol. 31, p. 704
  作者：Emilewicz、v. Kostanecki

  DOI：——

  日期：——