4-bromo-N-(4-formylphenyl)benzamide | 1312201-07-2

• 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: 4-bromo-N-(4-formylphenyl)benzamide
• CAS: 1312201-07-2
• 化学式: C₁₄H₁₀BrNO₂
• 分子量: 304.143
• InChiKey: DWQKPEAHQGQRFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-N-(4-formylphenyl)benzamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium periodate 、 potassium acetate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 (4-((4-formylphenyl)carbamoyl)phenyl)boronic acid
  参考文献：
  名称：

  Structure-Based Design of Novel Boronic Acid-Based Inhibitors of Autotaxin

  摘要：

  Autotaxin (ATX) is a secreted phosphodiesterase that hydrolyzes the abundant phospholipid lysophosphatidylcholine (LPC) to produce lysophosphatidic acid (LPA). The ATX-LPA signaling axis has been implicated in inflammation, fibrosis, and tumor progression, rendering ATX an attractive drug target. We recently described a boronic add-based inhibitor of ATX, named HA155 (1). Here, we report the design of new inhibitors based on the crystal structure of ATX in complex with inhibitor 1. Furthermore, we describe the syntheses and activities of these new inhibitors, whose potencies can be explained by structural data. To understand the difference in activity between two different isomers with nanomolar potencies, we performed molecular docking experiments. Intriguingly, molecular docking suggested a remarkable binding pose for one of the isomers, which differs from the original binding pose of inhibitor 1 for ATX, opening further options for inhibitor design.

  DOI：

  10.1021/jm200310q
• 作为产物：
  描述：

  4-(1,3-二氧戊环-2-基)苯胺 在 高氯酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-bromo-N-(4-formylphenyl)benzamide
  参考文献：
  名称：

  Structure-Based Design of Novel Boronic Acid-Based Inhibitors of Autotaxin

  摘要：

  Autotaxin (ATX) is a secreted phosphodiesterase that hydrolyzes the abundant phospholipid lysophosphatidylcholine (LPC) to produce lysophosphatidic acid (LPA). The ATX-LPA signaling axis has been implicated in inflammation, fibrosis, and tumor progression, rendering ATX an attractive drug target. We recently described a boronic add-based inhibitor of ATX, named HA155 (1). Here, we report the design of new inhibitors based on the crystal structure of ATX in complex with inhibitor 1. Furthermore, we describe the syntheses and activities of these new inhibitors, whose potencies can be explained by structural data. To understand the difference in activity between two different isomers with nanomolar potencies, we performed molecular docking experiments. Intriguingly, molecular docking suggested a remarkable binding pose for one of the isomers, which differs from the original binding pose of inhibitor 1 for ATX, opening further options for inhibitor design.

  DOI：

  10.1021/jm200310q

文献信息

• Synthesis and biological evaluation of novel 1,2,3,4-tetrahydro-β-carboline derivatives as potential antibacterial agents
  作者：Yuan-Ze Song、Juan Zhang、Qing-Jiang Song、Wen-Hao Zhu、Chao Yuan、Kai-Ming Wang、Cheng-Shi Jiang

  DOI：10.1016/j.bmcl.2024.129822

  日期：2024.9

  The quest for novel antibacterial agents is imperative in the face of escalating antibiotic resistance. Naturally occurring tetrahydro--carboline (THC) alkaloids have been highlighted due to their significant biological derivatives. However, these structures have been little explored for antibacterial drugs development. In this study, a series of 1,2,3,4-THC derivatives were synthesized and assessed

  面对不断升级的抗生素耐药性，寻找新型抗菌药物势在必行。天然存在的四氢咔啉 (THC) 生物碱因其重要的生物衍生物而受到关注。然而，这些结构在抗菌药物开发中的探索却很少。在这项研究中，合成了一系列 1,2,3,4-THC 衍生物，并评估了它们对革兰氏阳性菌和革兰氏阴性菌的抗菌能力。这些化合物表现出中等至良好的抗菌活性，其中一些化合物对革兰氏阳性菌，特别是耐甲氧西林 (MRSA) 的抗菌活性优于庆大霉素。在这些类似物中，该化合物成为热门化合物，表现出快速的杀菌作用和显着的抗菌后效应，对人LO2和HepG2细胞具有显着的细胞毒性。此外，在小鼠腹部感染模型中，化合物（10 mg/kg）显示出与环丙沙星（2 mg/kg）相当的抗 MRSA 功效。总体而言，目前的研究结果表明，基于标题化合物的 THC 衍生物在抗菌药物的开发中具有广阔的应用前景。