liquiritigenin 7,4′-diacetate | 59121-64-1

• 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: liquiritigenin 7,4′-diacetate
• 英文别名: 4',7-diacetoxyflavan-4-one；LTG 7,4′-diacetate；7-acetoxy-2-(4-acetoxy-phenyl)-chroman-4-one；7-Acetoxy-2-(4-acetoxy-phenyl)-chroman-4-on；Diacetyl-liquiritigenin；[4-(7-Acetoxy-4-oxo-chroman-2-yl)phenyl] acetate；[4-(7-acetyloxy-4-oxo-2,3-dihydrochromen-2-yl)phenyl] acetate
• CAS: 59121-64-1
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: ZXYRFBJRBWNPSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  liquiritigenin 7,4′-diacetate 在 palladium on activated charcoal 、 三氟化硼乙醚 、 水 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 C₂₄H₂₂O₆
  参考文献：
  名称：

  Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans

  摘要：

  Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3 center dot OEt2 catalyzed arylation reactions of 4',7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4',7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.117
• 作为产物：
  描述：

  异甘草素 在 吡啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 liquiritigenin 7,4′-diacetate
  参考文献：
  名称：

  酸催化黄酮的立体选择性重排和二聚：依赖素的合成

  摘要：

  当用甲醇盐酸处理时，适当取代的黄酮会发生立体选择性重排和二聚化，生成苯并吡喃基苯并吡喃。提出了重新安排的理由。该合成方法已用于天然产物依赖素的高产率合成。

  DOI：

  10.1016/j.tet.2007.03.173

文献信息

• Flavonoid Compounds and Uses Thereof
  申请人：Jarrott Bevyn

  公开号：US20090130051A1

  公开（公告）日：2009-05-21

  Novel flavonoid compounds having anti-oxidant activity are described. The compounds and compositions have been shown to exhibit anti-oxidant properties and are particularly useful in the treatment of ischemia and reperfusion injuries. The invention also describes a method to chemically synthesize such flavonoid compounds and test their efficacy. Such compounds and corresponding pharmaceutically acceptable derivatives and/or salts have uses in the areas of pharmaceuticals, nutraceutical, and veterinary applications.

  本发明描述了具有抗氧化活性的新型黄酮类化合物。这些化合物和组合物已被证明具有抗氧化性质，特别适用于缺血和再灌注损伤的治疗。本发明还描述了一种化学合成这种黄酮类化合物并测试其功效的方法。这些化合物及其对应的药学上可接受的衍生物和/或盐在制药、保健品和兽医应用领域中有用。
• Shinoda; Ueeda, Chemische Berichte, 1934, vol. 67, p. 434,439
  作者：Shinoda、Ueeda

  DOI：——

  日期：——
• In vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin
  作者：Rashmi Gaur、Kuldeep Singh Yadav、Ram Kishor Verma、Narayan Prasad Yadav、Rajendra Singh Bhakuni

  DOI：10.1016/j.phymed.2013.10.015

  日期：2014.3

  Isoliquiritigenin (ISL), a chalcone and liquiritigenin (LTG), a flavonoid found in licorice roots and several other plants. ISL displays antioxidant, anti-inflammatory, antitumor and hepatoprotective activities whereas LTG is an estrogenic compound, acts as an agonist selective for the beta-subtype of the oestrogen receptor. Both the phenolics were isolated from the rhizomes of Glycyrrhiza glabra. Five derivatives from ISL and four derivatives from LTG were synthesized. All the compounds were established by extensive spectroscopic analyses and screened through oral glucose tolerance test to gain preliminary information regarding the antihyperglycemic effect in normal Swiss albino male mice. ISL (1), ISL derivatives 3, 4, 5, 7 and LTG derivatives 9 and 10 showed significant blood glucose lowering effect. The structure-activity relationship indicated that the presence of ether and ester groups in ISL and LTG analogues are important for exhibiting the activity. Compounds 1,4 and 10 were selected for in vivo antidiabetic activity and found to be potential candidates for treatment of diabetes. It is the first report on antidiabetic activity of ISL derivative 4 and LTG derivative 10. (C) 2013 Elsevier GmbH. All rights reserved.
• FLAVONOID COMPOUNDS AND USES THEREOF
  申请人：Howard Florey Institute of Experimental Physiology and Medicine

  公开号：EP1856085A1

  公开（公告）日：2007-11-21
• US8017649B2
  申请人：——

  公开号：US8017649B2

  公开（公告）日：2011-09-13