methyl 2-(5-bromopyridin-3-yl)-3-(furan-2-yl)-3-oxopropanoate | 936371-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(5-bromopyridin-3-yl)-3-(furan-2-yl)-3-oxopropanoate
• CAS: 936371-69-6
• 化学式: C₁₃H₁₀BrNO₄
• 分子量: 324.131
• InChiKey: NNKDFKIPWJOUIG-UHFFFAOYSA-N

物化性质

• 沸点：
  426.6±40.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(5-bromopyridin-3-yl)-3-(furan-2-yl)-3-oxopropanoate 在 硫酸 作用下， 反应 10.0h， 以68%的产率得到2-(5-bromopyridin-3-yl)-1-(furan-2-yl)ethanone
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Inhibitors for Severe Acute Respiratory Syndrome 3C-Like Protease Based on Phthalhydrazide Ketones or Heteroaromatic Esters

  摘要：

  The 3C-like protease (3CL(pro)), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CL(pro) inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.

  DOI：

  10.1021/jm061425k
• 作为产物：
  描述：

  5-溴-3-吡啶基乙酸 在 氯化亚砜 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 methyl 2-(5-bromopyridin-3-yl)-3-(furan-2-yl)-3-oxopropanoate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Inhibitors for Severe Acute Respiratory Syndrome 3C-Like Protease Based on Phthalhydrazide Ketones or Heteroaromatic Esters

  摘要：

  The 3C-like protease (3CL(pro)), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CL(pro) inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.

  DOI：

  10.1021/jm061425k

文献信息

• Design, Synthesis, and Evaluation of Inhibitors for Severe Acute Respiratory Syndrome 3C-Like Protease Based on Phthalhydrazide Ketones or Heteroaromatic Esters
  作者：Jianmin Zhang、Hanna I. Pettersson、Carly Huitema、Chunying Niu、Jiang Yin、Michael N. G. James、Lindsay D. Eltis、John C. Vederas

  DOI：10.1021/jm061425k

  日期：2007.4.1

  The 3C-like protease (3CL(pro)), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CL(pro) inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.