7-hydroxy-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one

• 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-hydroxy-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one
• 英文别名: 7-Hydroxy-2-[2-(trifluoromethyl)phenyl]chromen-4-one
• 化学式: C₁₆H₉F₃O₃
• 分子量: 306.241
• InChiKey: GROMCRMFQUJQPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-hydroxy-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one 、 碘甲烷 在 potassium carbonate 作用下， 以91%的产率得到7-methoxy-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Inhibitory effect of flavonoids on human glutaminyl cyclase

  摘要：

  Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4' (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.064
• 作为产物：
  描述：

  4-(2-氯-1-亚氨基乙基)苯-1,3-二醇 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 7-hydroxy-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Inhibitory effect of flavonoids on human glutaminyl cyclase

  摘要：

  Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4' (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.064

文献信息

• Synthesis and Anti-cancer Activities of Apigenin Derivatives
  作者：Xing Zheng、Liuying Yu、Jing Yang、Xu Yao、Wenna Yan、Shaowei Bo、Ya Liu、Yun Wei、Zhiyi Wu、Guan Wang

  DOI：10.2174/1573406410666140307152557

  日期：2014.3.7

  A novel series of apigenin derivatives with phloroglucinol or resorcinol as raw materials were synthesized according to Baker-Venaktaraman reaction and their in vitro inhibitory activities on colorectal adenocarcinoma (HT-29) and leucocythemia (HL-60) cell lines were evaluated by the standard methyl thiazole tetrazolium (MTT) method. The results of biological test showed that some of apigenin derivatives possessed stronger anti-cancer activities than apigenin. Compound 6 showed the strongest activity against colorectal adenocarcinoma (HT-29) and leucocythemia (HL-60) cell lines with IC50 valure of 2.03±0.22 µM, 2.25±0.42 µM, it was better than 5-FU (12.92±0.61 µM, 9.56±0.16 µM), which shows a potential compound for colorectal adenocarcinoma and leucocythemia.

  根据贝克-维纳克塔拉曼反应合成了一系列新型芹菜素衍生物，并以氯代葡萄糖苷醇或间苯二酚为原料，采用标准甲基噻唑四氮唑（MTT）法评价了它们对结直肠腺癌（HT-29）和白血病（HL-60）细胞株的体外抑制活性。生物测试结果表明，一些芹菜素衍生物比芹菜素具有更强的抗癌活性。化合物 6 对结直肠腺癌（HT-29）和白血病（HL-60）细胞株的活性最强，其 IC50 值分别为 2.03±0.22 µM、2.25±0.42 µM，优于 5-FU（12.92±0.61 µM、9.56±0.16 µM），这表明该化合物具有治疗结直肠腺癌和白血病的潜力。
• Inhibitory effect of flavonoids on human glutaminyl cyclase
  作者：Manman Li、Yao Dong、Xi Yu、Yongdong Zou、Yizhi Zheng、Xianzhang Bu、Junmin Quan、Zhendan He、Haiqiang Wu

  DOI：10.1016/j.bmc.2016.03.064

  日期：2016.5

  Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4' (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC. (C) 2016 Elsevier Ltd. All rights reserved.