5-Bromopyridin-3-yl furan-2-carboxylate | 936371-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-Bromopyridin-3-yl furan-2-carboxylate
• 英文别名: (5-bromopyridin-3-yl) furan-2-carboxylate
• CAS: 936371-58-3
• 化学式: C₁₀H₆BrNO₃
• 分子量: 268.067
• InChiKey: HMICIXHTRIFAET-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±32.0 °C(Predicted)
• 密度：
  1.624±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Bromopyridin-3-yl furan-2-carboxylate 在 4-二甲氨基吡啶 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 生成 5-bromopyridin-3-yl dimethylcarbamate
  参考文献：
  名称：

  用吡啶靶向 S1 位点的 SARS-CoV-2 主蛋白酶酰化和共价可逆片段抑制剂的关键研究

  摘要：

  在寻找合适的 SARS-CoV-2 M pro S1 结合片段时，测试了具有不同接头（L、X）的吡啶-亲电试剂组合的活性、动力学和化学稳定性。卤代吡啶酯显示出高活性但缺乏稳定性，而吡啶醛片段似乎具有进一步药物开发的潜力。

  DOI：

  10.1002/cmdc.202200635
• 作为产物：
  描述：

  糠酸（呋喃甲酸） 在 N,N-二甲基甲酰胺 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 5-Bromopyridin-3-yl furan-2-carboxylate
  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

• Structure–activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors
  作者：Isak Im、Eui Seung Lee、Soo Jeong Choi、Ju-Yeon Lee、Yong-Chul Kim

  DOI：10.1016/j.bmcl.2009.04.114

  日期：2009.7

  Human rhinovirus 3C protease (HRV 3C(pro)) is known to be a promising target for development of therapeutic agents against the common cold because of the importance of the protease in viral replication as well as its expression in a large number of serotypes. To explore non-peptidic inhibitors of HRV 3C(pro), a series of novel heteroaromatic esters was synthesized and evaluated for inhibitory activity against HRV 3C(pro), to determine the structure-activity relationships. The most potent inhibitor, 7, with a 5-bromopyridinyl group, had an IC50 value of 80 nM. In addition, the binding mode of a novel analog, 19, with the 4-hydroxyquinolinone moiety, was explored by molecular docking, suggesting a new interaction in the S1 pocket. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• A Critical Study on Acylating and Covalent Reversible Fragment Inhibitors of SARS‐CoV‐2 Main Protease Targeting the S1 Site with Pyridine
  作者：Rebekka Wamser、Szymon Pach、Christoph Arkona、Morris Baumgardt、Umer Bin Abdul Aziz、Andreas C. Hocke、Gerhard Wolber、Jörg Rademann

  DOI：10.1002/cmdc.202200635

  日期：——

  In the search for suitable S1 binding fragments of SARS-CoV-2 Mpro, pyridine-electrophile combinations with different linkers (L, X) were tested regarding their activity, kinetics and chemical stability. Halopyridinyl esters showed high activity but lacked in stability, while pyridine aldehyde fragments seem to have the potential for further drug development.

  在寻找合适的 SARS-CoV-2 M pro S1 结合片段时，测试了具有不同接头（L、X）的吡啶-亲电试剂组合的活性、动力学和化学稳定性。卤代吡啶酯显示出高活性但缺乏稳定性，而吡啶醛片段似乎具有进一步药物开发的潜力。