2-amino-6-iodo-3-(2-(trifluoromethyl)phenyl)quinazolin-4(3H)-one | 1383992-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-amino-6-iodo-3-(2-(trifluoromethyl)phenyl)quinazolin-4(3H)-one
• 英文别名: 2-amino-6-iodo-3-[2-(trifluoromethyl)phenyl]-4(3H)-quinazolinone；2-Amino-6-iodo-3-[2-(trifluoromethyl)phenyl]quinazolin-4-one
• CAS: 1383992-02-6
• 化学式: C₁₅H₉F₃IN₃O
• 分子量: 431.156
• InChiKey: CCNWCXTUJFJACH-UHFFFAOYSA-N

物化性质

• 沸点：
  509.1±60.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-fluorophenyl)-2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide 、 2-amino-6-iodo-3-(2-(trifluoromethyl)phenyl)quinazolin-4(3H)-one 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以19.48%的产率得到5-(2-amino-3-(2-(trifluoromethyl)phenyl)-4-oxo-3,4-dihydroquinazolin-6-yl)-N-(3-fluorophenyl)-2-methoxypyridine-3-sulfonamide
  参考文献：
  名称：

  [EN] QUINAZOLINONE DERIVATIVES AS ANTIVIRAL AGENTS
  [FR] DÉRIVÉS DE QUINAZOLINONE EN TANT QU'AGENTS ANTIVIRAUX

  摘要：

  提供了化合物及其药用盐，它们的药物组合物，它们的制备方法，以及它们用于治疗由黄病毒科（Flaviviridae）家族成员介导的病毒感染，如丙型肝炎病毒（HCV）的用途。

  公开号：

  WO2012087938A1
• 作为产物：
  描述：

  6-iodo-2-thioxo-3-(2-(trifluoromethyl)phenyl)-2,3-dihydroquinazolin-4(1H)-one 在 五氯化磷 、 N,N-二异丙基乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 2-amino-6-iodo-3-(2-(trifluoromethyl)phenyl)quinazolin-4(3H)-one
  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] QUINAZOLINONE DERIVATIVES AS ANTIVIRAL AGENTS<br/>[FR] DÉRIVÉS DE QUINAZOLINONE EN TANT QU'AGENTS ANTIVIRAUX
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012087938A1

  公开（公告）日：2012-06-28

  Provided are compounds and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

  提供了化合物及其药用盐，它们的药物组合物，它们的制备方法，以及它们用于治疗由黄病毒科（Flaviviridae）家族成员介导的病毒感染，如丙型肝炎病毒（HCV）的用途。