N-(4-benzothiazol-2-yl-phenyl)-2-(3-methoxyphenoxy)acetamide | 1388658-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-(4-benzothiazol-2-yl-phenyl)-2-(3-methoxyphenoxy)acetamide
• 英文别名: N-[4-(1,3-benzothiazol-2-yl)phenyl]-2-(3-methoxyphenoxy)acetamide
• CAS: 1388658-04-5
• 化学式: C₂₂H₁₈N₂O₃S
• 分子量: 390.463
• InChiKey: FYJKPCFYYJGKDO-UHFFFAOYSA-N

物化性质

• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

制备方法与用途

BDM31827是一种乙醇脱氢酶（EthR）抑制剂。

反应信息

• 作为产物：
  描述：

  4-(2-苯并噻唑基)苯胺 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 N-(4-benzothiazol-2-yl-phenyl)-2-(3-methoxyphenoxy)acetamide
  参考文献：
  名称：

  Synthesis of some N-[4-(benzothiazole-2yl) phenyl]-2-aryloxyacetamide derivatives and their anticancer activities

  摘要：

  In this study, some N-[4-(Benzothiazole-2-yl)phenyl]-2-aryloxyacetamide derivatives were prepared by reacting N-[4-(benzothiazole-2yl)phenyl]-2-chloroacetamide and different substituent phenol or thiophenol derivatives. The anticancer activities of the compounds obtained were investigated. It was observed that some of the compounds, namely 25 and 38, showed notable anticancer activity.

  DOI：

  10.3109/14756366.2011.599030

文献信息

• Discovery of Novel <i>N</i>-Phenylphenoxyacetamide Derivatives as EthR Inhibitors and Ethionamide Boosters by Combining High-Throughput Screening and Synthesis
  作者：Marion Flipo、Nicolas Willand、Nathalie Lecat-Guillet、Candide Hounsou、Matthieu Desroses、Florence Leroux、Zoé Lens、Vincent Villeret、Alexandre Wohlkönig、René Wintjens、Thierry Christophe、Hee Kyoung Jeon、Camille Locht、Priscille Brodin、Alain R Baulard、Benoit Déprez

  DOI：10.1021/jm300377g

  日期：2012.7.26

  In this paper, we describe the screening of a 14640-compound library using a novel whole mycobacteria phenotypic assay to discover inhibitors of EthR, a transcriptional repressor implicated in the innate resistance of Mycobacterium tuberculosis to the second-line antituberculosis drug ethionamide. From this screening a new chemical family of EthR inhibitors bearing an N-phenylphenoxyacetamide motif was identified. The X-ray structure of the most potent compound crystallized with EthR inspired the synthesis of a 960-member focused library. These compounds were tested in vitro using a rapid thermal shift assay on EthR to accelerate the optimization. The best compounds were synthesized on a larger scale and confirmed as potent ethionamide boosters on M. tuberculosis-infected macrophages. Finally, the cocrystallization of the best optimized analogue with EthR revealed an unexpected reorientation of the ligand in the binding pocket.
• Synthesis of some N-[4-(benzothiazole-2yl) phenyl]-2-aryloxyacetamide derivatives and their anticancer activities
  作者：Funda Tay、Leyla Yurttaş、Şeref Demirayak

  DOI：10.3109/14756366.2011.599030

  日期：2012.8.1

  In this study, some N-[4-(Benzothiazole-2-yl)phenyl]-2-aryloxyacetamide derivatives were prepared by reacting N-[4-(benzothiazole-2yl)phenyl]-2-chloroacetamide and different substituent phenol or thiophenol derivatives. The anticancer activities of the compounds obtained were investigated. It was observed that some of the compounds, namely 25 and 38, showed notable anticancer activity.