1-[4-(4-chloro-benzoyloxy)-2-hydroxy-phenyl]-3-(4-chloro-phenyl)-propane-1,3-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 1-[4-(4-chloro-benzoyloxy)-2-hydroxy-phenyl]-3-(4-chloro-phenyl)-propane-1,3-dione
• 英文别名: 1-[4-(4-Chlor-benzoyloxy)-2-hydroxy-phenyl]-3-(4-chlor-phenyl)-propan-1,3-dion；[4-[3-(4-Chlorophenyl)-3-oxopropanoyl]-3-hydroxyphenyl] 4-chlorobenzoate
• 化学式: C₂₂H₁₄Cl₂O₅
• 分子量: 429.256
• InChiKey: GAAOTWJMUAOYQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[4-(4-chloro-benzoyloxy)-2-hydroxy-phenyl]-3-(4-chloro-phenyl)-propane-1,3-dione 在 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 生成 7-(3-bromopropoxy)-2-(4-chlorophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new arylpiperazine derivatives bearing a flavone moiety as α1-adrenoceptor antagonists

  摘要：

  Elaborate study on the three-dimensional model of alpha(1)-adrenoceptor (alpha(1)-AR) antagonists led to the development of a series of new arylpiperazine derivatives bearing a flavone nucleus as alpha(1)-AR antagonists. The in vitro activities were evaluated and compounds 1, 4, 10, 13 and 15 showed activities close to the reference compound (Prazosin). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.080
• 作为产物：
  描述：

  2',4'-bis(4-chlorobenzoyloxy)acetophenone 在 吡啶 、 potassium carbonate 作用下， 生成 1-[4-(4-chloro-benzoyloxy)-2-hydroxy-phenyl]-3-(4-chloro-phenyl)-propane-1,3-dione
  参考文献：
  名称：

  Dunne et al., Journal of the Chemical Society, 1950, p. 1252,1257

  摘要：

  DOI：

文献信息

• An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids
  作者：X. Wang、J. Liu、Y. Zhang

  DOI：10.1134/s1070363218050328

  日期：2018.5

  A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity

  使用修饰的Baker-Venkataraman反应，由2-羟基苯乙酮合成了许多4'-取代的（R = H，Me，Cl，F）黄酮衍生物。首次合成化合物[3-（4-氟苯甲酰基）-5-羟基-4'-氟黄酮]，产率为12％。抗增殖试验表明，合成的黄酮在4'位具有F取代基，显示出比其他黄酮衍生物更高的活性，特别是针对HeLa和MCF-7的IC 50为9.5和2.7μM。
• Synthesis of Flavonoid 7-<i>O</i>-β-D-glycosides by Phase Transfer Catalysis
  作者：Zheng Wu、Ling Jiang、He Chen、Qiu-an Wang

  DOI：10.3184/030823409x431346

  日期：2009.3

  Six flavonoid 7- O-β-D-glycosides 1a-3a and 1b–3b were synthesised from the flavones 7a and 7b by glycosidation and deacetylation with the corresponding α-acetylglycosyl bromides. 7a and 7b were prepared in high yield by an improved Baker-Venkataraman rearrangement using 2, 4-dihydroxyacetophenone as starting material and tetrabutylammonium bromide (TBAB) as a phase transfer catalyst. The glycosidation procedure was modified by using anhydrous K₂CO₃ in a solvent mixture of DMF/acetone (3:2v/v) and TBAB as a phase transfer catalyst.

  以黄酮 7a 和 7b 为原料，通过糖苷化和相应的 α-乙酰糖基溴化物脱乙酰化合成了六种黄酮 7- O-β-D 糖苷 1a-3a 和 1b-3b。以 2，4-二羟基苯乙酮为起始原料，以四丁基溴化铵（TBAB）为相转移催化剂，通过改进的贝克-文卡塔拉曼重排法高产制备了 7a 和 7b。通过在 DMF/ 丙酮（3:2v/v）混合溶剂中使用无水 K2CO3 和 TBAB 作为相转移催化剂，对糖苷化过程进行了改进。
• Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation
  作者：Honghui Liu、Yan Wang、Mingxia Lv、Yi Luo、Bu-Ming Liu、Yan Huang、Mian Wang、Jianyi Wang

  DOI：10.1016/j.bioorg.2020.104370

  日期：2020.12

  A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC₅₀ = 1.343 µM) and L12 (IC₅₀ = 1.207 µM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.