1-(2',4'-dihydroxyphenyl)-3-(4''-methylphenyl)-propane-1,3-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2',4'-dihydroxyphenyl)-3-(4''-methylphenyl)-propane-1,3-dione
• 英文别名: 1-(2,4-Dihydroxyphenyl)-3-(4-methylphenyl)propane-1,3-dione
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: IMQLDLZGRRFZQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2',4'-dihydroxyphenyl)-3-(4''-methylphenyl)-propane-1,3-dione 在 硫酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 7-hydroxy-2-(p-tolyl)-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
• 作为产物：
  描述：

  2',4'-bis(4-methylbenzoyloxy)acetophenone 在 sodium hydroxide 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以72%的产率得到1-(2',4'-dihydroxyphenyl)-3-(4''-methylphenyl)-propane-1,3-dione
  参考文献：
  名称：

  Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3-aryl-propane-1,3-diones

  摘要：

  This research communication is toward the investigation of the antibacterial, antifungal and antioxidant activities of the synthesized compounds 1-(4'-O-beta-D-glucopyranosyloxy-2'-hydroxyphenyl)-3-aryl-propane-1,3-diones (5a)-(5h). These compounds have been obtained by the interaction of alpha-acetobromoglucose with 1-(2',4'-dihydroxyphenyl)-3-aryl-propane-1,3-diones (3a)-(3h) under anhydrous condition and at lower temperature. The structures of these newly synthesized O-beta-D-glucopyranosides were established on the basis of chemical, elemental, and spectral analyses. Further, the compounds (5b), (5c), (5d) and (5g) showed potent antibacterial and antifungal activity. A good correlation was obtained between the theoretical predictions of bioavailability using Lipinski's rule-of-five and experimental verification. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.068