N-hydroxy-5-nitrobenzo[b]thiophene-2-carboxamide | 914606-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-hydroxy-5-nitrobenzo[b]thiophene-2-carboxamide
• 英文别名: 5-Nitrobenzothiophene-2-carbohydroxamic acid；N-hydroxy-5-nitro-1-benzothiophene-2-carboxamide
• CAS: 914606-01-2
• 化学式: C₉H₆N₂O₄S
• 分子量: 238.224
• InChiKey: RKTDJVVWLDJJQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-硝基苯并[b]噻吩-2-羧酸甲酯 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以92%的产率得到N-hydroxy-5-nitrobenzo[b]thiophene-2-carboxamide
  参考文献：
  名称：

  Hydroxamic Acids Block Replication of Hepatitis C Virus

  摘要：

  Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structureactivity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.

  DOI：

  10.1021/jm501330g

文献信息

• Hydroxamic Acids Block Replication of Hepatitis C Virus
  作者：Teng Ai、Yanli Xu、Li Qiu、Robert J. Geraghty、Liqiang Chen

  DOI：10.1021/jm501330g

  日期：2015.1.22

  Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structureactivity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.