2-chloro-N-(3,4-dichloro-phenyl)propionamide | 25251-76-7

• 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: 2-chloro-N-(3,4-dichloro-phenyl)propionamide
• 英文别名: 2-chloro-N-(3,4-dichlorophenyl)propanamide
• CAS: 25251-76-7
• 化学式: C₉H₈Cl₃NO
• mdl: MFCD09971920
• 分子量: 252.528
• InChiKey: DAFPFECFVGRHLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(3,4-dichloro-phenyl)propionamide 、 potassium thioacyanate 生成 3',4'-Dichlor-2-thiocyanatopropionanilid
  参考文献：
  名称：

  Synthesis of new antimicrobials. III. Synthesis of chlorine-substituted 4-thiocyanatoaniline and 2-amino-6-chlorobenzothiazole derivatives.

  摘要：

  为了检验它们的抗菌活性，合成了氯取代的4-硫氰基苯胺（A）和2-氨基-6-氯苯噻唑（B）的新的N-衍生物，这些衍生物是通过化合物A或B与卤乙酰卤、烷基氯甲酸酯、苯氧乙酰氯、苯基异氰酸酯或芳醛反应得到的。

  DOI：

  10.1248/cpb.23.659
• 作为产物：
  描述：

  2-氯丙酰氯 、 3,4-二氯苯胺 以 N,N-二甲基乙酰胺 为溶剂， 反应 96.0h， 以64%的产率得到2-chloro-N-(3,4-dichloro-phenyl)propionamide
  参考文献：
  名称：

  Discovery of Novel N-Phenylphenoxyacetamide Derivatives as EthR Inhibitors and Ethionamide Boosters by Combining High-Throughput Screening and Synthesis

  摘要：

  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.

  DOI：

  10.1021/jm300377g

文献信息

• Synthesis of 4,6-Dimethylpyrimidine 2-Thiosubstituted Derivatives and Their Preliminary Biological Evaluation
  作者：Aleksandr P. Yengoyan、Elen N. Hambardzumyan、Asya S. Vorskanyan、Lusya V. Shahbazyan

  DOI：10.2174/1570178617999200601165334

  日期：2021.3