2-phenyl-5-(4-trifluoromethylphenyl)-1,4-benzoquinone | 1301629-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-5-(4-trifluoromethylphenyl)-1,4-benzoquinone
• 英文别名: 2-phenyl-5-[4-(trifluoromethyl)phenyl]cyclohexa-2,5-diene-1,4-dione
• CAS: 1301629-96-8
• 化学式: C₁₉H₁₁F₃O₂
• 分子量: 328.29
• InChiKey: AYAFQQLEQMIVCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenyl-5-(4-trifluoromethylphenyl)-1,4-benzoquinone 、 乙酸酐 在 sodium acetate 、 锌 作用下， 反应 1.5h， 以26%的产率得到acetic acid 5'-acetoxy-4-trifluoromethyl-[1,1';4',1'']terphenyl-2'-yl ester
  参考文献：
  名称：

  Synthesis and evaluation of arylquinones as BACE1 inhibitors, β-amyloid peptide aggregation inhibitors, and destabilizers of preformed β-amyloid fibrils

  摘要：

  BACE1 activity, inhibition of A beta aggregation, and disaggregation of preformed A beta fibrils constitute the three major targets in the development of small-molecule lipophilic new drugs for the treatment of Alzheimer's disease (AD). Quinones are widely distributed among natural products and possess relevant and varied biological activities including antitumor and antibiotic, inhibition of HIV-1 reverse transcriptase, antidiabetic, or COX-inhibition, among others. We report herein the interaction of several arylquinones and their derivatives with the amyloidogenic pathway of the amyloid precursor protein processing. Our studies put forward that these compounds are promising candidates in the development of new drugs which are effective simultaneously towards the three major targets of AD. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.023
• 作为产物：
  描述：

  4-三氟甲基苯硼酸 、 苯基-P-苯醌 在 palladium(II) trifluoroacetate 、 silver trifluoromethanesulfonate 、 iron(III) chloride hexahydrate 作用下， 以 四氢呋喃 、 水 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 2-phenyl-5-(4-trifluoromethylphenyl)-1,4-benzoquinone 、 2-phenyl-6-(4-trifluoromethylphenyl)-1,4-benzoquinone
  参考文献：
  名称：

  Synthesis and evaluation of arylquinones as BACE1 inhibitors, β-amyloid peptide aggregation inhibitors, and destabilizers of preformed β-amyloid fibrils

  摘要：

  BACE1 activity, inhibition of A beta aggregation, and disaggregation of preformed A beta fibrils constitute the three major targets in the development of small-molecule lipophilic new drugs for the treatment of Alzheimer's disease (AD). Quinones are widely distributed among natural products and possess relevant and varied biological activities including antitumor and antibiotic, inhibition of HIV-1 reverse transcriptase, antidiabetic, or COX-inhibition, among others. We report herein the interaction of several arylquinones and their derivatives with the amyloidogenic pathway of the amyloid precursor protein processing. Our studies put forward that these compounds are promising candidates in the development of new drugs which are effective simultaneously towards the three major targets of AD. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.023

文献信息

• Synthesis and evaluation of arylquinones as BACE1 inhibitors, β-amyloid peptide aggregation inhibitors, and destabilizers of preformed β-amyloid fibrils
  作者：Andrea Ortega、Ángela Rincón、Karim L. Jiménez-Aliaga、Paloma Bermejo-Bescós、Sagrario Martín-Aragón、María Teresa Molina、Aurelio G. Csákÿ

  DOI：10.1016/j.bmcl.2011.03.023

  日期：2011.4

  BACE1 activity, inhibition of A beta aggregation, and disaggregation of preformed A beta fibrils constitute the three major targets in the development of small-molecule lipophilic new drugs for the treatment of Alzheimer's disease (AD). Quinones are widely distributed among natural products and possess relevant and varied biological activities including antitumor and antibiotic, inhibition of HIV-1 reverse transcriptase, antidiabetic, or COX-inhibition, among others. We report herein the interaction of several arylquinones and their derivatives with the amyloidogenic pathway of the amyloid precursor protein processing. Our studies put forward that these compounds are promising candidates in the development of new drugs which are effective simultaneously towards the three major targets of AD. (C) 2011 Elsevier Ltd. All rights reserved.