4-N-butyl-6-fluoroquinazoline-2,4-diamine | 1413944-34-9

• 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: 4-N-butyl-6-fluoroquinazoline-2,4-diamine
• CAS: 1413944-34-9
• 化学式: C₁₂H₁₅FN₄
• 分子量: 234.276
• InChiKey: HFEFNYOZNORHRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸甲酯 在 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-N-butyl-6-fluoroquinazoline-2,4-diamine
  参考文献：
  名称：

  Discovery of selective 2,4-diaminoquinazoline toll-like receptor 7 (TLR 7) agonists

  摘要：

  The discovery of a novel series of highly potent quinazoline TLR 7/8 agonists is described. The synthesis and structure-activity relationship is presented. Structural requirements and optimization of this series toward TLR 7 selectivity afforded the potent agonist 48. Pharmacokinetic and pharmacodynamic studies highlighted 48 as an orally available endogenous interferon (IFN-alpha) inducer in mice. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.01.014

文献信息

• [EN] QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF VIRAL INFECTIONS AND FURTHER DISEASES<br/>[FR] DÉRIVÉS DE QUINAZOLINE POUR LE TRAITEMENT D'INFECTIONS VIRALES ET D'AUTRES MALADIES
  申请人：JANSSEN R & D IRELAND

  公开号：WO2012156498A1

  公开（公告）日：2012-11-22

  This invention relates to quinazoline derivatives, processes for their preparation, pharmaceutical compositions, and their use in therapy of disorders in which the modulation of toll - like - receptors is involved.

  这项发明涉及喹唑啉衍生物，其制备方法，药物组合物以及它们在调节类似于toll受体参与的疾病治疗中的用途。
• QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF VIRAL INFECTIONS AND FURTHER DISEASES
  申请人：McGowan David

  公开号：US20140073642A1

  公开（公告）日：2014-03-13

  This invention relates to quinazoline derivatives, processes for their preparation, pharmaceutical compositions, and their use in therapy of disorders in which the modulation of toll-like-receptors is involved.

  这项发明涉及喹唑啉衍生物，其制备方法，药物组合物以及它们在调节Toll样受体参与的疾病治疗中的应用。
• US8916575B2
  申请人：——

  公开号：US8916575B2

  公开（公告）日：2014-12-23
• Discovery of selective 2,4-diaminoquinazoline toll-like receptor 7 (TLR 7) agonists
  作者：Serge Pieters、David McGowan、Florence Herschke、Frederik Pauwels、Bart Stoops、Stefaan Last、Werner Embrechts、Annick Scholliers、Wendy Mostmans、Kris Van Dijck、Bertrand Van Schoubroeck、Tine Thoné、Dorien De Pooter、Gregory Fanning、Mari Luz Rosauro、Mourad Daoubi Khamlichi、Ioannis Houpis、Eric Arnoult、Tim H.M. Jonckers、Pierre Raboisson

  DOI：10.1016/j.bmcl.2018.01.014

  日期：2018.2

  The discovery of a novel series of highly potent quinazoline TLR 7/8 agonists is described. The synthesis and structure-activity relationship is presented. Structural requirements and optimization of this series toward TLR 7 selectivity afforded the potent agonist 48. Pharmacokinetic and pharmacodynamic studies highlighted 48 as an orally available endogenous interferon (IFN-alpha) inducer in mice. (C) 2018 Elsevier Ltd. All rights reserved.