N-hydroxy-N-(1-(5-butylfur-2-yl)ethyl) urea

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-hydroxy-N-(1-(5-butylfur-2-yl)ethyl) urea
• 英文别名: N-[1-(5-butyl-2-furyl)ethyl]-N-hydroxyurea；1-[1-(5-butylfuran-2-yl)ethyl]-1-hydroxyurea
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: YZFZZHNVTXWCDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  79.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(5-Butyl-furan-2-yl)-ethanone oxime 在 盐酸 、 吡啶硼烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.17h， 生成 N-hydroxy-N-(1-(5-butylfur-2-yl)ethyl) urea
  参考文献：
  名称：

  Structure−Activity Relationships of N-Hydroxyurea 5-Lipoxygenase Inhibitors

  摘要：

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.

  DOI：

  10.1021/jm9700474

文献信息

• Substituted furan compounds which are useful in inhibiting lipoxygenase enzymes, particularly 5-lipoxygenase
  申请人：ABBOTT LABORATORIES

  公开号：EP0320628B1

  公开（公告）日：1997-01-15
• FURAN AND PYRROLE CONTAINING LIPOXYGENASE INHIBITING COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP0388429A1

  公开（公告）日：1990-09-26
• EP0388429A4
  申请人：——

  公开号：EP0388429A4

  公开（公告）日：1991-08-21
• US5112848A
  申请人：——

  公开号：US5112848A

  公开（公告）日：1992-05-12
• WO1989004299A1
  申请人：——

  公开号：WO1989004299A1

  公开（公告）日：1989-05-18