5,7-dihydroxy-2-(3',4'-difluorophenyl)chromone | 673475-86-0

• 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: 5,7-dihydroxy-2-(3',4'-difluorophenyl)chromone
• 英文别名: 2-(3,4-Difluorophenyl)-5,7-dihydroxy-chromen-4-one；2-(3,4-difluorophenyl)-5,7-dihydroxychromen-4-one
• CAS: 673475-86-0
• 化学式: C₁₅H₈F₂O₄
• 分子量: 290.223
• InChiKey: BRBZAOQGHDVSQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 吡啶 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 24.0h， 生成 5,7-dihydroxy-2-(3',4'-difluorophenyl)chromone
  参考文献：
  名称：

  Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor

  摘要：

  Novel chromone derivatives with a benzopyran-4-one scaffold have been prepared by the one-pot cyclization reaction. The in vitro inhibitory activity of these new compounds towards HIV-1 protease have been evaluated using stop time HPLC method as the preliminary screening. The most potent compound, 7,8-dihydroxy-2-(3'-trifluoromethyl phenyl)-3-(3 ''-trifluoromethylbenzoyl)chromone (32), showed IC50 = 0.34 mu M. The molecular docking study supported results from experimental activity testing and also provided structure-activity relationship of this series. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.06.035

文献信息

• Antimalarial activity of HIV-1 protease inhibitor in chromone series
  作者：Pradith Lerdsirisuk、Chirattikan Maicheen、Jiraporn Ungwitayatorn

  DOI：10.1016/j.bioorg.2014.10.006

  日期：2014.12

  Increasing parasite resistance to nearly all available antimalarial drugs becomes a serious problem to human health and necessitates the need to continue the search for new effective drugs. Recent studies have shown that clinically utilized HIV-1 protease (HIV-1 PR) inhibitors can inhibit the in vitro and in vivo growth of Plasmodium falciparum. In this study, a series of chromone derivatives possessing HIV-1 PR inhibitory activity has been tested for antimalarial activity against P. falciparum (K1 multi-drug resistant strain). Chromone 15, the potent HIV-1 PR inhibitor (IC50 = 0.65 mu M), was found to be the most potent antimalarial compound with IC50 = 0.95 mu M while primaquine and tafenoquine showed IC50 = 2.41 and 1.95 mu M, respectively. Molecular docking study of chromone compounds against plasmepsin II, an aspartic protease enzyme important in hemoglobin degradation, revealed that chromone 15 exhibited the higher binding affinity (binding energy = -13.24 kcal/mol) than the known PM II inhibitors. Thus, HIV-1 PR inhibitor in chromone series has the potential to be a new class of antimalarial agent. (C) 2014 Elsevier Inc. All rights reserved.