7-(2-(cyclohexylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one | 1236122-81-8

• 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-(2-(cyclohexylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
• 英文别名: 7-[2-(Cyclohexylamino)ethoxy]-5-hydroxy-2-phenylchromen-4-one
• CAS: 1236122-81-8
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: BAHVRONKKLSZIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

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 7-(2-(cyclohexylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of Some New Chrysin Derivatives and Their Biological Assessment as Antibacterial, Antibiofilm and Antifungal Agent

  摘要：

  一些新的天然黄酮衍生物已经合成并评估了其抗菌、抗生物膜和抗真菌活性。三种化合物，即2a、2e和2i在六种细菌和两种真菌类型菌株中显示出优异的活性（MIC 14.0-18.3 μg/mL），而大多数其他化合物的活性则相对较低到中等。对于导致肺炎的两种细菌菌株，2a、2e和2i也显示出显著的抗生物膜和杀菌活性（MBC范围为17-20 μg/mL）。本研究进一步表明，具有7-O-烷基取代的黄酮化合物比相应的芳基取代同类物更为有效，这表明黄酮的7-O位点对抗微生物活性至关重要。因此，本文将有助于通过对天然黄酮的结构调制，进一步设计和开发潜在的抗微生物剂，而天然黄酮是一种具有多种生物活性的潜在分子骨架。

  DOI：

  10.14233/ajchem.2018.21167

文献信息

• 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.
• Synthesis of Some New Chrysin Derivatives and Their Biological Assessment as Antibacterial, Antibiofilm and Antifungal Agent
  作者：S. Bhowmik、T. Das、S. Ghosh、B.K. Sharma、S. Majumdar、U.C. De

  DOI：10.14233/ajchem.2018.21167

  日期：——

  Some new derivatives of natural chrysin have been synthesized and evaluated for antibacterial, antibiofilm and antifungal activities. Three compounds, namely 2a, 2e, 2i showed excellent activities (MIC 14.0-18.3 μg/mL) against six bacterial and two fungal type strains while most of the other compounds showed comparatively low to moderate values of such activities. Significant antibiofilm and bactericidal activities (MBC ranges from 17-20 μg/mL) were also observed for 2a, 2e, 2i against pneumonia causing two bacterial strains. This study further indicated that the chrysin compounds with 7-O-alkyl type substitution were much more effective than corresponding aryl substituted congeners which signifies that 7-O position of chrysin is crucial for antimicrobial activities. Thus, this article would contribute to further design and development of potential antimicrobial agents via structural modulation of natural chrysin, which is a potential molecular skeleton with diverse biological activities.

  一些新的天然黄酮衍生物已经合成并评估了其抗菌、抗生物膜和抗真菌活性。三种化合物，即2a、2e和2i在六种细菌和两种真菌类型菌株中显示出优异的活性（MIC 14.0-18.3 μg/mL），而大多数其他化合物的活性则相对较低到中等。对于导致肺炎的两种细菌菌株，2a、2e和2i也显示出显著的抗生物膜和杀菌活性（MBC范围为17-20 μg/mL）。本研究进一步表明，具有7-O-烷基取代的黄酮化合物比相应的芳基取代同类物更为有效，这表明黄酮的7-O位点对抗微生物活性至关重要。因此，本文将有助于通过对天然黄酮的结构调制，进一步设计和开发潜在的抗微生物剂，而天然黄酮是一种具有多种生物活性的潜在分子骨架。