(2E)-3-(5-bromo-2-hydroxyphenyl)-1-(1H-indol-2-yl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-3-(5-bromo-2-hydroxyphenyl)-1-(1H-indol-2-yl)prop-2-en-1-one
• 英文别名: (E)-3-(5-bromo-2-hydroxyphenyl)-1-(1H-indol-2-yl)prop-2-en-1-one
• 化学式: C₁₇H₁₂BrNO₂
• 分子量: 342.192
• InChiKey: AEJSYWFSIMVPNP-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基吲哚 、 5-溴水杨醛 在 苄基三甲基氢氧化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以33%的产率得到(2E)-3-(5-bromo-2-hydroxyphenyl)-1-(1H-indol-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents

  摘要：

  Several novel series of compounds were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK has been identified as a highly interconnected essential 'hub' protein in MRSA, with structural features distinct from the human homologs which makes it a novel antimicrobial target. Several MRSA PK inhibitors (including the hydrazide 1) were identified using in silico screening combined with enzyme assays and were found to be selective for bacterial enzyme compared to human PK isoforms. Structure-activity relationship (SAR) studies were carried out on the replacement of the hydrazide linker with 3-atoms, 2-atoms and 0-atom linkers and led us to discover more potent compounds with enzyme inhibiting activities in the low nanomolar range and some were found to effectively inhibit bacteria growth in culture with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.018

文献信息

• Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents
  作者：Christophe Labrière、Huansheng Gong、B. Brett Finlay、Neil E. Reiner、Robert N. Young

  DOI：10.1016/j.ejmech.2016.09.018

  日期：2017.1

  Several novel series of compounds were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK has been identified as a highly interconnected essential 'hub' protein in MRSA, with structural features distinct from the human homologs which makes it a novel antimicrobial target. Several MRSA PK inhibitors (including the hydrazide 1) were identified using in silico screening combined with enzyme assays and were found to be selective for bacterial enzyme compared to human PK isoforms. Structure-activity relationship (SAR) studies were carried out on the replacement of the hydrazide linker with 3-atoms, 2-atoms and 0-atom linkers and led us to discover more potent compounds with enzyme inhibiting activities in the low nanomolar range and some were found to effectively inhibit bacteria growth in culture with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. (C) 2016 Elsevier Masson SAS. All rights reserved.