N-(5-bromopyridin-3-yl)furan-2-carboxamide | 1448807-22-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(5-bromopyridin-3-yl)furan-2-carboxamide
• CAS: 1448807-22-4
• 化学式: C₁₀H₇BrN₂O₂
• 分子量: 267.082
• InChiKey: KPNBEISHYHGLTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-bromopyridin-3-yl)furan-2-carboxamide 、 噁唑并[4,5-b]吡啶 在 palladium diacetate 、 caesium carbonate 、 copper(I) bromide 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以17%的产率得到N-(5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)furan-2-carboxamide
  参考文献：
  名称：

  3-(Oxazolo[4,5-b]pyridin-2-yl)anilides as a novel class of potent inhibitors for the kinetoplastid Trypanosoma brucei, the causative agent for human African trypanosomiasis

  摘要：

  A whole organism high-throughput screen of approximately 87,000 compounds against Trypanosoma brucei brucei led to the recent discovery of several novel compound classes with low micromolar activity against this organism and without appreciable cytotoxicity to mammalian cells. Herein we report a structure activity relationship (SAR) investigation around one of these hit classes, the 3-(oxazolo[4,5-b] pyridin-2-yl)anilides. Sharp SAR is revealed, with our most active compound (5) exhibiting an IC50 of 91 nM against the human pathogenic strain T.b. rhodesiense and being more than 700 times less toxic towards the L6 mammalian cell line. Physicochemical properties are attractive for many compounds in this series. For the most potent representatives, we show that solubility and metabolic stability are key parameters to target during future optimisation.[GRAPHICS](C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.05.007
• 作为产物：
  描述：

  5-溴-3-氨基吡啶 、 糠酸（呋喃甲酸） 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以9%的产率得到N-(5-bromopyridin-3-yl)furan-2-carboxamide
  参考文献：
  名称：

  3-(Oxazolo[4,5-b]pyridin-2-yl)anilides as a novel class of potent inhibitors for the kinetoplastid Trypanosoma brucei, the causative agent for human African trypanosomiasis

  摘要：

  A whole organism high-throughput screen of approximately 87,000 compounds against Trypanosoma brucei brucei led to the recent discovery of several novel compound classes with low micromolar activity against this organism and without appreciable cytotoxicity to mammalian cells. Herein we report a structure activity relationship (SAR) investigation around one of these hit classes, the 3-(oxazolo[4,5-b] pyridin-2-yl)anilides. Sharp SAR is revealed, with our most active compound (5) exhibiting an IC50 of 91 nM against the human pathogenic strain T.b. rhodesiense and being more than 700 times less toxic towards the L6 mammalian cell line. Physicochemical properties are attractive for many compounds in this series. For the most potent representatives, we show that solubility and metabolic stability are key parameters to target during future optimisation.[GRAPHICS](C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.05.007

文献信息

• 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。
• 3-(Oxazolo[4,5-b]pyridin-2-yl)anilides as a novel class of potent inhibitors for the kinetoplastid Trypanosoma brucei, the causative agent for human African trypanosomiasis
  作者：Lori Ferrins、Raphaël Rahmani、Melissa L. Sykes、Amy J. Jones、Vicky M. Avery、Eliott Teston、Basmah Almohaywi、JieXiang Yin、Jason Smith、Chris Hyland、Karen L. White、Eileen Ryan、Michael Campbell、Susan A. Charman、Marcel Kaiser、Jonathan B. Baell

  DOI：10.1016/j.ejmech.2013.05.007

  日期：2013.8

  A whole organism high-throughput screen of approximately 87,000 compounds against Trypanosoma brucei brucei led to the recent discovery of several novel compound classes with low micromolar activity against this organism and without appreciable cytotoxicity to mammalian cells. Herein we report a structure activity relationship (SAR) investigation around one of these hit classes, the 3-(oxazolo[4,5-b] pyridin-2-yl)anilides. Sharp SAR is revealed, with our most active compound (5) exhibiting an IC50 of 91 nM against the human pathogenic strain T.b. rhodesiense and being more than 700 times less toxic towards the L6 mammalian cell line. Physicochemical properties are attractive for many compounds in this series. For the most potent representatives, we show that solubility and metabolic stability are key parameters to target during future optimisation.[GRAPHICS](C) 2013 Published by Elsevier Masson SAS.