3-[(3-chlorobenzyl)oxy]benzamide

• 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: 3-[(3-chlorobenzyl)oxy]benzamide
• 英文别名: 3-[(3-chlorophenyl)methoxy]benzamide
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: OAXJYKCTIPZAMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-羟基苯甲酰氯 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-[(3-chlorobenzyl)oxy]benzamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel FtsZ‐targeted 3‐arylalkoxy‐2,6‐difluorobenzamides as Potential Antimicrobial Agents

  摘要：

  Novel series of 3‐O‐arylalkylbenzamide and 3‐O‐arylalkyl‐2,6‐difluorobenzamide derivatives were synthesized and evaluated for their on‐target activity and antibacterial activity. The results indicated that the 3‐O‐arylalkyl‐2,6‐difluorobenzamide derivatives possessed much better on‐target activity and antibacterial activity than the 3‐O‐arylalkylbenzamide derivatives. Among them, 3‐O‐chlorobenzyl derivative 36 was the most effective in antibacterial activity (0.5, 4, and 8 μg/mL) against Bacillus subtilis ATCC9372, methicillin‐resistant Staphylococcus aureus ATCC29213, and penicillin‐resistant Staphylococcus aureus PR, while 3‐O‐methylbenzyl derivative 41 only exhibited the most potent activity (2 μg/mL) against Staphylococcus aureus ATCC25923.

  DOI：

  10.1111/cbdd.12658

文献信息

• Targeting the FtsZ Allosteric Binding Site with a Novel Fluorescence Polarization Screen, Cytological and Structural Approaches for Antibacterial Discovery
  作者：Sonia Huecas、Lidia Araújo-Bazán、Federico M. Ruiz、Laura B. Ruiz-Ávila、R. Fernando Martínez、Andrea Escobar-Peña、Marta Artola、Henar Vázquez-Villa、Mar Martín-Fontecha、Carlos Fernández-Tornero、María L. López-Rodríguez、José M. Andreu

  DOI：10.1021/acs.jmedchem.0c02207

  日期：2021.5.13

  for discovering new antibiotics. Binding of small molecules to the cleft between the N-terminal guanosine triphosphate (GTP)-binding and the C-terminal subdomains allosterically impairs the FtsZ function, eventually inhibiting bacterial division. Nonetheless, the lack of appropriate chemical tools to develop a binding screen against this site has hampered the discovery of FtsZ antibacterial inhibitors

  细菌对抗生素的耐药性使以前可控制的感染再次致残和致死，凸显了对新抗菌策略的需求。在这方面，通过靶向关键蛋白 FtsZ 来抑制细菌分裂过程已被认为是发现新抗生素的有吸引力的方法。小分子与 N 端三磷酸鸟苷 (GTP) 结合和 C 端亚结构域之间的裂缝结合会变构损害 FtsZ 功能，最终抑制细菌分裂。尽管如此，缺乏适当的化学工具来开发针对该位点的结合筛选阻碍了 FtsZ 抗菌抑制剂的发现。在这里，我们描述了第一个竞争性结合测定，以识别与域间裂缝相互作用的 FtsZ 变构配体，基于使用特定的高亲和力荧光探针。这种新颖的分析与表型分析和 X 射线晶体学见解一起，能够鉴定和表征细菌分裂的 FtsZ 抑制剂，旨在发现更有效的抗菌剂。
• CASEIN KINASE 1delta (CK 1delta) INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODE-GENERATIVE DISEASES SUCH AS TAUOPATHIES
  申请人：Sheridan Joseph M.

  公开号：US20140031547A1

  公开（公告）日：2014-01-30

  The invention relates to pharmaceutical compositions comprising casein kinase 1 delta (CK1δ) and to the use of said inhibitors in the treatment of neurodegenerative disorders such as Alzheimer's disease.
• CASEIN KINASE 1delta (CK 1delta) INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES SUCH AS TAUOPATHIES
  申请人：Electrophoretics Limited

  公开号：US20160354375A1

  公开（公告）日：2016-12-08

  The invention relates to pharmaceutical compositions comprising casein kinase 1 delta (CK1δ) and to the use of said inhibitors in the treatment of neurodegenerative disorders such as Alzheimer's disease.
• Synthesis and Biological Evaluation of Novel FtsZ‐targeted 3‐arylalkoxy‐2,6‐difluorobenzamides as Potential Antimicrobial Agents
  作者：Shengsheng Qiang、Changde Wang、Henrietta Venter、Xin Li、Yi Wang、Liwei Guo、Ruixin Ma、Shutao Ma

  DOI：10.1111/cbdd.12658

  日期：2016.2

  Novel series of 3‐O‐arylalkylbenzamide and 3‐O‐arylalkyl‐2,6‐difluorobenzamide derivatives were synthesized and evaluated for their on‐target activity and antibacterial activity. The results indicated that the 3‐O‐arylalkyl‐2,6‐difluorobenzamide derivatives possessed much better on‐target activity and antibacterial activity than the 3‐O‐arylalkylbenzamide derivatives. Among them, 3‐O‐chlorobenzyl derivative 36 was the most effective in antibacterial activity (0.5, 4, and 8 μg/mL) against Bacillus subtilis ATCC9372, methicillin‐resistant Staphylococcus aureus ATCC29213, and penicillin‐resistant Staphylococcus aureus PR, while 3‐O‐methylbenzyl derivative 41 only exhibited the most potent activity (2 μg/mL) against Staphylococcus aureus ATCC25923.