5,6,7-trihydroxy-3-phenyl-chromen-4-one | 22137-61-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,6,7-trihydroxy-3-phenyl-chromen-4-one
• 英文别名: 5,6,7-Trihydroxy-3-phenyl-chromen-4-on；5,6,7-Trihydroxyisoflavone；5,6,7-trihydroxy-3-phenylchromen-4-one
• CAS: 22137-61-7
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: AIXGIDCHNCBENY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6,7-trihydroxy-3-phenyl-chromen-4-one 在 盐酸 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 丙酮 、 sodium iodide 作用下， 生成 5,7-diacetoxy-6-methoxy-3-phenyl-chromen-4-one
  参考文献：
  名称：

  异黄酮的环-异构体变化：5,7-二甲氧基-6-羟基异黄酮，muningin和5,7-二羟基-6-甲氧基异黄酮的合成

  摘要：

  上述化合物已经通过涉及从更容易获得的5,7,8-取代的异黄酮进行异构体改变的方法制备。

  DOI：

  10.1016/0040-4020(59)80054-5
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 甲酸 、 三氟化硼乙醚 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.75h， 生成 5,6,7-trihydroxy-3-phenyl-chromen-4-one
  参考文献：
  名称：

  α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors

  摘要：

  The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyi-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively/ (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.010

文献信息

• Chromones and chromone derivatives and uses thereof
  申请人：Yen Mao-Hsiung

  公开号：US20060142211A1

  公开（公告）日：2006-06-29

  The present invention relates to chromones, novel chromone derivatives, and pharmaceutical formulations containing the same and methods of use thereof. Uses of the present invention include, but are not limited to, use for the prevention and treatment of septic shock, organ injury and other disorders. The compounds described herein can be salt forms and also water-soluble compounds.

  本发明涉及香豆素，新型香豆素衍生物，以及含有它们的制药配方和使用方法。本发明的用途包括但不限于预防和治疗败血性休克、器官损伤和其他疾病。所述化合物可以是盐形式和水溶性化合物。
• Aghoramurthy et al., Journal Of Scientific and Industrial Research, 1956, vol. 15 B, p. 11
  作者：Aghoramurthy et al.

  DOI：——

  日期：——
• Karmarkar et al., Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 660,662
  作者：Karmarkar et al.

  DOI：——

  日期：——
• Mahesh et al., Proceedings - Indian Academy of Sciences, Section A, 1954, # 39, p. 165,174
  作者：Mahesh et al.

  DOI：——

  日期：——
• Dhar; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1956, # 43, p. 79,81
  作者：Dhar、Seshadri

  DOI：——

  日期：——