4-(2-amino-5-bromo-3-pyridyl)phenol | 1314883-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(2-amino-5-bromo-3-pyridyl)phenol
• 英文别名: 4-(2-Amino-5-bromopyridin-3-yl)phenol
• CAS: 1314883-36-7
• 化学式: C₁₁H₉BrN₂O
• 分子量: 265.109
• InChiKey: XACWVYOYIIFUOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：
  59.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-amino-5-bromo-3-pyridyl)phenol 、 4-羟基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以71%的产率得到4,4'-(2-aminopyridine-3,5-diyl)diphenol
  参考文献：
  名称：

  Development of Pyridine-based Inhibitors for the Human Vaccinia-related Kinases 1 and 2

  摘要：

  Vaccinia-related kinases 1 and 2 (VRK1 and VRK2) are human Ser/Thr protein kinases associated with increased cell division and neurological disorders. Nevertheless, the cellular functions of these proteins are not fully understood. Despite their therapeutic potential, there are no potent and specific inhibitors available for VRK1 or VRK2. We report here the discovery and elaboration of an aminopyridine scaffold as a basis for VRK1 and VRK2 inhibitors. The most potent compound for VRK1 (26) displayed an IC50 value of 150 nM and was fairly selective in a panel of 48 human kinases (selectivity score S(50%) of 0.04). Differences in compound binding mode and substituent preferences between the two VRKs were identified by the structure-activity relationship combined with the crystallographic analysis of key compounds. We expect our results to serve as a starting point for the design of more specific and potent inhibitors against each of the two VRKs.

  DOI：

  10.1021/acsmedchemlett.9b00082
• 作为产物：
  描述：

  2-氨基-5-溴-3-碘吡啶 、 4-羟基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 4-(2-amino-5-bromo-3-pyridyl)phenol
  参考文献：
  名称：

  Development of Pyridine-based Inhibitors for the Human Vaccinia-related Kinases 1 and 2

  摘要：

  Vaccinia-related kinases 1 and 2 (VRK1 and VRK2) are human Ser/Thr protein kinases associated with increased cell division and neurological disorders. Nevertheless, the cellular functions of these proteins are not fully understood. Despite their therapeutic potential, there are no potent and specific inhibitors available for VRK1 or VRK2. We report here the discovery and elaboration of an aminopyridine scaffold as a basis for VRK1 and VRK2 inhibitors. The most potent compound for VRK1 (26) displayed an IC50 value of 150 nM and was fairly selective in a panel of 48 human kinases (selectivity score S(50%) of 0.04). Differences in compound binding mode and substituent preferences between the two VRKs were identified by the structure-activity relationship combined with the crystallographic analysis of key compounds. We expect our results to serve as a starting point for the design of more specific and potent inhibitors against each of the two VRKs.

  DOI：

  10.1021/acsmedchemlett.9b00082

文献信息

• NEW ANTI-MALARIAL AGENTS
  申请人：Witty Michael John

  公开号：US20120295905A1

  公开（公告）日：2012-11-22

  The present invention is related to a use of aminopyridine derivatives in the manufacture of a medicament for preventing or treating malaria. Specifically, the present invention is related to aminopyridine derivatives useful for the preparation of a pharmaceutical formulation for the inhibition of malaria parasite proliferation.

  本发明涉及氨基吡啶衍生物在制造预防或治疗疟疾药物方面的用途。具体而言，本发明涉及氨基吡啶衍生物，可用于制备制药配方，以抑制疟原虫的增殖。
• US9024033B2
  申请人：——

  公开号：US9024033B2

  公开（公告）日：2015-05-05
• [EN] NEW ANTI-MALARIAL AGENTS<br/>[FR] NOUVEAUX AGENTS ANTIPALUDIQUES
  申请人：MEDICINES FOR MALARIA VENTURE MMV

  公开号：WO2011086531A2

  公开（公告）日：2011-07-21

  The present invention is related to a use of aminopyridine derivatives in the manufacture of a medicament for preventing or treating malaria. Specifically, the present invention is related to aminopyridine derivatives useful for the preparation of a pharmaceutical formulation for the inhibition of malaria parasite proliferation.
• Development of Pyridine-based Inhibitors for the Human Vaccinia-related Kinases 1 and 2
  作者：Ricardo A. M. Serafim、Fernando H. de Souza Gama、Luiz A. Dutra、Caio V. dos Reis、Stanley N. S. Vasconcelos、André da Silva Santiago、Jéssica E. Takarada、Fúlvia Di Pillo、Hatylas Azevedo、Alessandra Mascarello、Jonathan M. Elkins、Katlin B. Massirer、Opher Gileadi、Cristiano R. W. Guimarães、Rafael M. Couñago

  DOI：10.1021/acsmedchemlett.9b00082

  日期：2019.9.12

  Vaccinia-related kinases 1 and 2 (VRK1 and VRK2) are human Ser/Thr protein kinases associated with increased cell division and neurological disorders. Nevertheless, the cellular functions of these proteins are not fully understood. Despite their therapeutic potential, there are no potent and specific inhibitors available for VRK1 or VRK2. We report here the discovery and elaboration of an aminopyridine scaffold as a basis for VRK1 and VRK2 inhibitors. The most potent compound for VRK1 (26) displayed an IC50 value of 150 nM and was fairly selective in a panel of 48 human kinases (selectivity score S(50%) of 0.04). Differences in compound binding mode and substituent preferences between the two VRKs were identified by the structure-activity relationship combined with the crystallographic analysis of key compounds. We expect our results to serve as a starting point for the design of more specific and potent inhibitors against each of the two VRKs.