7-hydroxy-2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one | 127590-86-7

• 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-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one
• 英文别名: 4H-1-Benzopyran-4-one, 7-hydroxy-2-[4-(trifluoromethyl)phenyl]-；7-hydroxy-2-[4-(trifluoromethyl)phenyl]chromen-4-one
• CAS: 127590-86-7
• 化学式: C₁₆H₉F₃O₃
• 分子量: 306.241
• InChiKey: YXAVDUCTQODQKN-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-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 bis(4-oxo-2-(4-trifluoromethylphenyl)-4H-chromen-7-yl) methyl thiophosphate
  参考文献：
  名称：

  基于磷酸盐和硫代磷酸黄酮类似物的类固醇硫酸酯酶抑制剂。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21281
• 作为产物：
  描述：

  1-(2,4-Dihydroxy-phenyl)-3-(4-trifluoromethyl-phenyl)-propane-1,3-dione 在 硫酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 7-hydroxy-2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  A rational approach to the design of flavones as xanthine oxidase inhibitors

  摘要：

  In the light of previous QSAR studies on flavones as inhibitors of xanthine oxidase, we synthesized and tested a new series of 7-hydroxyflavones carrying a wide and balanced variety of substituents (pi, sigma(p)) at the 4' position in order to explore the effect of substituents at this position on the xanthine oxidase inhibitory activity. The results of pK(a) determinations show that the electronic effects of the substituents are not transferred to the hydroxyl at C7, previously found to be fundamental for activity. An excellent correlation is found between molar refractivity of the substituents and the inhibitory activity. These results, applied to the more active 5,7-dihydroxyflavones, allowed the design and synthesis of a very active inhibitor, with an IC50 in the nanomolar range. On interpretative grounds, C4' substituents of flavones are involved in dispersion interactions with the enzyme. The calculation of quantum chemical polarizabilities and solvent accessible surface areas suggests the existence of pi-pi stacking interactions with an aromatic aminoacidic residue of the enzyme.

  DOI：

  10.1016/0223-5234(96)85878-8

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。
• Synthesis and anticancer effect of B-Ring trifluoromethylated flavonoids
  作者：Xing Zheng、Jian-Guo Cao、Wei-Dong Meng、Feng-Ling Qing

  DOI：10.1016/s0960-894x(03)00752-2

  日期：2003.10

  A series of B-ring trifluoromethylated flavonoids derivatives were prepared and tested in vitro against human gastric adenocarcinoma cell line (SGC-7901). Among these derivatives, 5,7-dipropoxy-2-(4'-trifluoromethylphenyl)-chromen-4-one 5c had the strongest activity against SGC-7901 cell.

  制备了一系列B环三氟甲基化类黄酮衍生物，并在体外针对人胃腺癌细胞系（SGC-7901）进行了测试。在这些衍生物中，5，7-二丙氧基-2-（4'-三氟甲基苯基）-铬-4--4-酮5c对SGC-7901细胞具有最强的活性。
• Formation of the unexpected 3-alkylated flavonoids in the alkylation of B-ring substituted 5,7-dihydroxy flavones
  作者：Cai-Ling Wang、Xing Zheng、Wei-Dong Meng、Hong-Qi Li、Feng-Ling Qing

  DOI：10.1016/j.tetlet.2005.05.144

  日期：2005.8

  Treatment of B-ring substituted 5,7-dihydroxy flavones with alkyl halides in the presence of potassium carbonate gave unexpected 3-alkylated flavonoids. Related experiments were carried out to explain the formation of 3-alkylated flavonoids and a ring opening followed by alkylation and ring closure mechanism was proposed. (c) 2005 Elsevier Ltd. All rights reserved.
• Steroid Sulfatase Inhibitors Based on Phosphate and Thiophosphate Flavone Analogs
  作者：Witold Kozak、Mateusz Daśko、Maciej Masłyk、Konrad Kubiński、Janusz Rachon、Sebastian Demkowicz

  DOI：10.1002/ddr.21281

  日期：2015.12

  Preclinical Research

  临床前研究
• A rational approach to the design of flavones as xanthine oxidase inhibitors
  作者：L Costantino、G Rastelli、A Albasini

  DOI：10.1016/0223-5234(96)85878-8

  日期：1996.1

  In the light of previous QSAR studies on flavones as inhibitors of xanthine oxidase, we synthesized and tested a new series of 7-hydroxyflavones carrying a wide and balanced variety of substituents (pi, sigma(p)) at the 4' position in order to explore the effect of substituents at this position on the xanthine oxidase inhibitory activity. The results of pK(a) determinations show that the electronic effects of the substituents are not transferred to the hydroxyl at C7, previously found to be fundamental for activity. An excellent correlation is found between molar refractivity of the substituents and the inhibitory activity. These results, applied to the more active 5,7-dihydroxyflavones, allowed the design and synthesis of a very active inhibitor, with an IC50 in the nanomolar range. On interpretative grounds, C4' substituents of flavones are involved in dispersion interactions with the enzyme. The calculation of quantum chemical polarizabilities and solvent accessible surface areas suggests the existence of pi-pi stacking interactions with an aromatic aminoacidic residue of the enzyme.