5-hydroxy-2-phenyl-7-(2-(piperazin-1-yl)ethoxy)-4H-chromen-4-one | 1190373-61-5

• 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-hydroxy-2-phenyl-7-(2-(piperazin-1-yl)ethoxy)-4H-chromen-4-one
• 英文别名: 7-(2-(piperazin-1-yl)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one；5-hydroxy-2-phenyl-7-(2-piperazin-1-ylethoxy)chromen-4-one
• CAS: 1190373-61-5
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: CVHNMBUBVLEZOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  白杨素 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 24.0h， 生成 5-hydroxy-2-phenyl-7-(2-(piperazin-1-yl)ethoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel chrysin derivatives

  摘要：

  A series of chrysin derivatives 8a-8v were prepared and tested in vitro against HCT-116 (human colon cancer cell line), Hela (human cervical carcinoma cell line), DU-145 (human prostate cell line), K562 (human leukemia cell line), and SGC-7901 (human gastric cancer cell line). The chemical structures of these compounds were confirmed by means of MS, IR, H-1 NMR, C-13 NMR, and elemental analysis. Among these derivatives, 7-(2-(piperazin-1-yl)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, 8n, had the strongest activity against HCT-116, Hela, DU-145, K562, and SGC-7901 cells.

  DOI：

  10.1007/s00044-010-9395-1

文献信息

• Synthesis of C(7) modified chrysin derivatives designing to inhibit β-ketoacyl-acyl carrier protein synthase III (FabH) as antibiotics
  作者：Huan-Qiu Li、Lei Shi、Qing-Shan Li、Peng-Gang Liu、Yin Luo、Jing Zhao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.07.046

  日期：2009.9.1

  synthase III (FabH) catalyzes the initial step of fatty acid biosynthesis via a type II fatty acid synthase in most bacteria. The important role of this essential enzyme combined with its unique structural features and ubiquitous occurrence in bacteria has made it an attractive new target for the development of antibacterial agents. We first used a structure-based approach to develop 18 novel chrysin analogues

  作为天然分布的黄酮，菊花素具有多种生物活性，包括抗癌，抗炎和抗菌活性。β-酮酰基-酰基载体蛋白合酶III（FabH）在大多数细菌中通过II型脂肪酸合酶催化脂肪酸生物合成的起始步骤。这种必不可少的酶的重要作用，加上其独特的结构特征和在细菌中的普遍存在，使其成为开发抗菌剂的有吸引力的新目标。我们首先使用基于结构的方法来开发针对FabH的18种新的菊花素类似物，以开发新的抗生素。基于结构的设计方法被用于扩展菊花链衍生物，包括分子对接和SAR研究。根据结果​​，3克）显示出与1.56-6.25微克/毫升的MIC的最有效的抗菌活性对测试细菌的污渍，和对接模拟进行到位置化合物3克到大肠埃希氏 杆菌的FabH活性位点，以确定可能的结合构象。该生物测定表明，化合物3克是的有效抑制剂E. 大肠杆菌的FabH如抗生素。
• Synthesis and cytotoxicity of novel chrysin derivatives
  作者：Kun Hu、Wei Wang、Hong Cheng、ShaSha Pan、Jie Ren

  DOI：10.1007/s00044-010-9395-1

  日期：2011.9

  A series of chrysin derivatives 8a-8v were prepared and tested in vitro against HCT-116 (human colon cancer cell line), Hela (human cervical carcinoma cell line), DU-145 (human prostate cell line), K562 (human leukemia cell line), and SGC-7901 (human gastric cancer cell line). The chemical structures of these compounds were confirmed by means of MS, IR, H-1 NMR, C-13 NMR, and elemental analysis. Among these derivatives, 7-(2-(piperazin-1-yl)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, 8n, had the strongest activity against HCT-116, Hela, DU-145, K562, and SGC-7901 cells.