tert-butyl 3-(3-methylbenzo[b]thiophen-2-yl)azetidine-1-carboxylate | 1621696-73-8

• 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: tert-butyl 3-(3-methylbenzo[b]thiophen-2-yl)azetidine-1-carboxylate
• CAS: 1621696-73-8
• 化学式: C₁₇H₂₁NO₂S
• 分子量: 303.425
• InChiKey: GLVQPEIIBRSGFK-UHFFFAOYSA-N

物化性质

• 沸点：
  432.4±45.0 °C(predicted)
• 密度：
  1.197±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(3-methylbenzo[b]thiophen-2-yl)azetidine-1-carboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (E)-6-(3-(3-(3-methylbenzo[b]thiophen-2-yl)azetidin-1-yl)-3-oxoprop-1-en-1-yl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Discovery of azetidine based ene-amides as potent bacterial enoyl ACP reductase (FabI) inhibitors

  摘要：

  A novel and potent series of ene-amides featuring azetidines has been developed as FabI inhibitors active against drug resistant Gram-positive pathogens particularly staphylococcal organisms. Most of the compounds from the series possessed excellent biochemical inhibition of Staphylococcus aureus FabI enzyme and whole cell activity against clinically relevant MRSA, MSSA and MRSE organisms which are responsible for significant morbidity and mortality in community as well as hospital settings. The binding mode of one of the leads, AEA16, in Escherichia coli FabI enzyme was determined unambiguously using X-ray crystallography. The lead compounds displayed good metabolic stability in mice liver microsomes and pharmacokinetic profile in mice. The in vivo efficacy of lead AEA16 has been demonstrated in a lethal murine systemic infection model.

  DOI：

  10.1016/j.ejmech.2014.07.036
• 作为产物：
  描述：

  3-甲基苯噻吩 、 1-Boc-3-碘氮杂环丁烷 在 ferrous(II) sulfate heptahydrate 、 硫酸 、 双氧水 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 生成 tert-butyl 3-(3-methylbenzo[b]thiophen-2-yl)azetidine-1-carboxylate
  参考文献：
  名称：

  Discovery of azetidine based ene-amides as potent bacterial enoyl ACP reductase (FabI) inhibitors

  摘要：

  A novel and potent series of ene-amides featuring azetidines has been developed as FabI inhibitors active against drug resistant Gram-positive pathogens particularly staphylococcal organisms. Most of the compounds from the series possessed excellent biochemical inhibition of Staphylococcus aureus FabI enzyme and whole cell activity against clinically relevant MRSA, MSSA and MRSE organisms which are responsible for significant morbidity and mortality in community as well as hospital settings. The binding mode of one of the leads, AEA16, in Escherichia coli FabI enzyme was determined unambiguously using X-ray crystallography. The lead compounds displayed good metabolic stability in mice liver microsomes and pharmacokinetic profile in mice. The in vivo efficacy of lead AEA16 has been demonstrated in a lethal murine systemic infection model.

  DOI：

  10.1016/j.ejmech.2014.07.036