3-amino-6-bromopicolinaldehyde | 1289168-26-8

• 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: 3-amino-6-bromopicolinaldehyde
• 英文别名: 3-Amino-6-bromopicolinaldehyde；3-amino-6-bromopyridine-2-carbaldehyde
• CAS: 1289168-26-8
• 化学式: C₆H₅BrN₂O
• 分子量: 201.023
• InChiKey: TZGOZPQFWHUZLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-6-bromopicolinaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium t-butanolate 、 锌 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 Methyl 4-[(6-amino-7-pentyl-1,5-naphthyridin-2-yl)methyl]benzoate
  参考文献：
  名称：

  [EN] PYRIDINE-2-AMINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION AND USE THEREOF
  [FR] DÉRIVÉ DE PYRIDINE-2-AMINE, COMPOSITION PHARMACEUTIQUE ET UTILISATION ASSOCIÉE
  [ZH] 吡啶-2-胺衍生物及其药物组合物和用途

  摘要：

  本发明公开了一种吡啶-2-胺衍生物及其药物组合物和用途。上述吡啶-2-胺衍生物可用作TLR8选择性激动剂，具有选择性高、活性强、安全性好的特点，可用于预防和/或治疗由TLR活性相关的疾病，例如，病原体感染引起或病原体感染相关的疾病、免疫性疾病、炎症和肿瘤，还可用于制备疫苗佐剂，增强免疫应答，具有较佳的应用前景和研发价值。

  公开号：

  WO2022143985A1
• 作为产物：
  描述：

  2,6-二溴-3-氨基吡啶 在 正丁基锂 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.92h， 生成 3-amino-6-bromopicolinaldehyde
  参考文献：
  名称：

  Discovery of Selective Small Molecule Type III Phosphatidylinositol 4-Kinase Alpha (PI4KIIIα) Inhibitors as Anti Hepatitis C (HCV) Agents

  摘要：

  Hepatitis C virus (HCV) assembles many host cellular proteins into unique membranous replication structures as a prerequisite for viral replication, and PI4KIII alpha is an essential component of these replication organelles. RNA interference of PI4KIII alpha results in a breakdown of this replication complex and cessation of HCV replication in Huh-7 cells. PI4KIII alpha is a lipid kinase that interacts with the HCV nonstructural SA protein (NS5A) and enriches the HCV replication complex with its product, phosphoinositol 4-phosphate (PI4P). Elevated levels of PI4P at the endoplasmic reticulum have been linked to HCV infection in the liver of HCV infected patients.(1) We investigated if small molecule inhibitors of PI4KIII alpha could inhibit HCV replication in vitro. The synthesis and structure activity relationships associated with the biological inhibition of PI4KIII alpha and HCV replication are described. These efforts quinazolinone 28 that displays high selectivity for PI4KIII alpha and potently inhibits HCV replication in vitro. led directly to identification of quinazolinone 28 that displays high selectivity for PI4KIII alpha and potently inhibits HCV replication in vitro.

  DOI：

  10.1021/jm400781h

文献信息

• Discovery of Selective Small Molecule Type III Phosphatidylinositol 4-Kinase Alpha (PI4KIIIα) Inhibitors as Anti Hepatitis C (HCV) Agents
  作者：Anna L. Leivers、Matthew Tallant、J. Brad Shotwell、Scott Dickerson、Martin R. Leivers、Octerloney B. McDonald、Jeff Gobel、Katrina L. Creech、Susan L. Strum、Amanda Mathis、Sabrinia Rogers、Chris B. Moore、Janos Botyanszki

  DOI：10.1021/jm400781h

  日期：2014.3.13

  Hepatitis C virus (HCV) assembles many host cellular proteins into unique membranous replication structures as a prerequisite for viral replication, and PI4KIII alpha is an essential component of these replication organelles. RNA interference of PI4KIII alpha results in a breakdown of this replication complex and cessation of HCV replication in Huh-7 cells. PI4KIII alpha is a lipid kinase that interacts with the HCV nonstructural SA protein (NS5A) and enriches the HCV replication complex with its product, phosphoinositol 4-phosphate (PI4P). Elevated levels of PI4P at the endoplasmic reticulum have been linked to HCV infection in the liver of HCV infected patients.(1) We investigated if small molecule inhibitors of PI4KIII alpha could inhibit HCV replication in vitro. The synthesis and structure activity relationships associated with the biological inhibition of PI4KIII alpha and HCV replication are described. These efforts quinazolinone 28 that displays high selectivity for PI4KIII alpha and potently inhibits HCV replication in vitro. led directly to identification of quinazolinone 28 that displays high selectivity for PI4KIII alpha and potently inhibits HCV replication in vitro.
• [EN] PYRIDINE-2-AMINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION AND USE THEREOF<br/>[FR] DÉRIVÉ DE PYRIDINE-2-AMINE, COMPOSITION PHARMACEUTIQUE ET UTILISATION ASSOCIÉE<br/>[ZH] 吡啶-2-胺衍生物及其药物组合物和用途
  申请人：[en]TSINGHUA UNIVERSITY;[zh]清华大学

  公开号：WO2022143985A1

  公开（公告）日：2022-07-07

  本发明公开了一种吡啶-2-胺衍生物及其药物组合物和用途。上述吡啶-2-胺衍生物可用作TLR8选择性激动剂，具有选择性高、活性强、安全性好的特点，可用于预防和/或治疗由TLR活性相关的疾病，例如，病原体感染引起或病原体感染相关的疾病、免疫性疾病、炎症和肿瘤，还可用于制备疫苗佐剂，增强免疫应答，具有较佳的应用前景和研发价值。