(E)-1-(3-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one | 38270-24-5

• 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: (E)-1-(3-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one
• 英文别名: (E)-3-(2-hydroxyphenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one
• CAS: 38270-24-5
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: KAMRNYCNWDARJA-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one 、 methylenedimethyl sulfurane 生成 (3-Methoxy-phenyl)-[2-(2-methoxy-phenyl)-cyclopropyl]-methanone
  参考文献：
  名称：

  MURPHY, W. S.;WATTANASIN, S., J. CHEM. SOC. PERKIN TRANS., 1981, N 11, 2920-2926

  摘要：

  DOI：
• 作为产物：
  描述：

  在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以75%的产率得到(E)-1-(3-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)

  摘要：

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).

  DOI：

  10.3109/14756366.2010.543420

文献信息

• Synthesis, Antimicrobial Activities, and Molecular Modeling Studies of Agents for the Sortase A Enzyme
  作者：Gizem Tatar Yilmaz、Nurettin Yayli、Tamer Tüzüner、Gözde Bozdal、Merve Salmanli、Gülin Renda、Büşra Korkmaz、Arif Bozdeveci、Şengül Alpay Karaoğlu

  DOI：10.1002/cbdv.202301659

  日期：2024.5

  Sortase A (SrtA) is an attractive target for developing new anti‐infective drugs that aim to interfere with essential virulence mechanisms, such as adhesion to host cells and biofilm formation. Herein, twenty hydroxy, nitro, bromo, fluoro, and methoxy substituted chalcone compounds were synthesized, antimicrobial activities and molecular modeling strategies against the SrtA enzyme were investigated. The most active compounds were found to be T2, T4, and T19 against Streptococcus mutans (S. mutans) with MIC values of 1.93, 3.8, 3.94 μg/mL, and docking scores of −6.46, −6.63, −6.73 kcal/mol, respectively. Also, these three active compounds showed better activity than the chlorohexidine (CHX) (MIC value: 4.88 μg/mL, docking score: −6.29 kcal/mol) in both in vitro and in silico. Structural stability and binding free energy analysis of S.mutans SrtA with active compounds were measured by molecular dynamic (MD) simulations throughout 100 nanoseconds (ns) time. It was observed that the stability of the critical interactions between these compounds and the target enzyme was preserved. To prove further, in vivo biological evaluation studies could be conducted for the most promising precursor compounds T2, T4, and T19, and it might open new avenues to the discovery of more potent SrtA inhibitors.