(2E)-1-(2',4',5'-trimethoxyphenyl)-3-[5-(2-chloro-5-trifluoromethylphenyl)-furan-2-yl]-2-propen-1-one | 1355970-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2E)-1-(2',4',5'-trimethoxyphenyl)-3-[5-(2-chloro-5-trifluoromethylphenyl)-furan-2-yl]-2-propen-1-one
• CAS: 1355970-39-6
• 化学式: C₂₃H₁₈ClF₃O₅
• 分子量: 466.841
• InChiKey: ZQPKPFDURVYSLB-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.9
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5-[2-氯-5-(三氟甲基)苯基]-2-呋喃甲醛 、 2′,4′,5′-三甲氧基苯乙酮 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以92%的产率得到(2E)-1-(2',4',5'-trimethoxyphenyl)-3-[5-(2-chloro-5-trifluoromethylphenyl)-furan-2-yl]-2-propen-1-one
  参考文献：
  名称：

  Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococcus aureus

  摘要：

  The increase in antibiotic resistance due to multiple factors has encouraged the search for new compounds which are active against multidrug-resistant pathogens. In this context, chalcones, dihydrochalcones, hydrazones and oxadiazoles were tested against Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus (MRSA) isolates, which were obtained from clinical laboratories and were characterized as MRSA using traditional and molecular methods. Among 65 tested compounds, two chalcones, one dihydrochalcone and two hydrazones were active against MRSA. Based on the minimal inhibitory concentration and cytotoxicity, hydrazones provided a better selectivity index than chalcones. Active hydrazones are promising antibiotic-like substances and they should be the subject of further microbiological studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.059

文献信息

• Synthetic compounds from an <i>in house</i> library as inhibitors of falcipain-2 from <i>Plasmodium falciparum</i>
  作者：Jean Borges Bertoldo、Louise Domeneghini Chiaradia-Delatorre、Alessandra Mascarello、Paulo César Leal、Marlon Norberto Sechini Cordeiro、Ricardo José Nunes、Emir Salas Sarduy、Philip Jon Rosenthal、Hernán Terenzi

  DOI：10.3109/14756366.2014.920839

  日期：2015.3.4

  Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkylesters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5 +/- 0.8 mu M, 9.5 +/- 0.2 mu M and 4.9 +/- 1.3 mu M, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.