N-hydroxy-N-(3-methylthien-2-yl)methyl urea

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-hydroxy-N-(3-methylthien-2-yl)methyl urea
• 英文别名: N-hydroxy-N-[(3-methylthien-2-yl)methyl]urea；1-hydroxy-1-[(3-methylthiophen-2-yl)methyl]urea
• 化学式: C₇H₁₀N₂O₂S
• 分子量: 186.235
• InChiKey: VTZSNBXHPCCGMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-methyl-2-thiophenecarboxaldoxime 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-(3-methylthien-2-yl)methyl 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

• UREA BASED LIPOXYGENASE INHIBITING COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP0588785A1

  公开（公告）日：1994-03-30
• EP0588785A4
  申请人：——

  公开号：EP0588785A4

  公开（公告）日：1991-12-30
• US5185363A
  申请人：——

  公开号：US5185363A

  公开（公告）日：1993-02-09
• [EN] UREA BASED LIPOXYGENASE INHIBITING COMPOUNDS
  申请人：——

  公开号：WO1990012008A1

  公开（公告）日：1990-10-18

  [EN] Substituted phenyl, naphthyl, and thienyl N-hydroxy urea compounds form a class of potent inhibitors of 5- and 12-lipoxygenase and are thus useful compounds in the treatment of inflammatory disease states where leukotrienes and other products of lipoxygenase enzyme activity are implicated.
  [FR] L'invention concerne des composés d'urée N-hydroxy de phényle, naphtyle et thiényle à substitution, formant une classe d'inhibiteurs puissants de lipoxygénase 5 et 12, utiles dans le traitement d'états inflammatoires dans lesquels des leucotriènes ainsi que d'autres produits présentant une activité enzymatique de lipoxygénase sont impliqués.