[4-(2-chloro-acetylamino)benzyl]carbamic acid tert-butyl ester | 917877-27-1

• 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-(2-chloro-acetylamino)benzyl]carbamic acid tert-butyl ester
• 英文别名: 1,1-Dimethylethyl N-[[4-[(2-chloroacetyl)amino]phenyl]methyl]carbamate；tert-butyl N-[[4-[(2-chloroacetyl)amino]phenyl]methyl]carbamate
• CAS: 917877-27-1
• 化学式: C₁₄H₁₉ClN₂O₃
• 分子量: 298.769
• InChiKey: QVQLJMFHVKOSAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [4-(2-chloro-acetylamino)benzyl]carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 2.0h， 以200 mg的产率得到p-(N-chloroacetamido)benzylamine hydrochloride
  参考文献：
  名称：

  Delivery of 2-5A cargo into living cells using the Tat cell penetrating peptide: 2-5A-tat

  摘要：

  2',5'-Oligoadenylate tetramer (2-5A) has been chemically conjugated to short HIV-1 Tat peptides to provide 2-5A-tat chimeras. Two different convergent synthetic approaches have been employed to provide such 2-5A-tat bioconjugates. One involved generation of a bioconjugate through reaction of a cysteine terminated Tat peptide with a alpha-chloroacetyl derivative of 2-5A. The second synthetic strategy was based upon a cycloaddition reaction of an azide derivative of 2-5A with a Tat peptide bearing an alkyne function. Either bioconjugate of 2-5A-tat was able to activate human RNase L. The union of 2-5A and Tat peptide provided an RNase L-active chimeric nucleopeptide with the ability to be taken up by cells by virtue of the Tat peptide and to activate RNase L in intact cells. This strategy provides a valuable vehicle for the entry of the charged 2-5A molecule into cells and may provide a means for targeted destruction of HIV RNA in vivo. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.058
• 作为产物：
  描述：

  氯乙酰氯 、 4-(N-BOC-氨甲基)苯胺 以 N,N-二甲基乙酰胺 为溶剂， 以84%的产率得到[4-(2-chloro-acetylamino)benzyl]carbamic acid tert-butyl ester
  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