N-hydroxy-N-(1-fur 2-ylethyl) 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-(1-fur 2-ylethyl) urea
• 英文别名: N-hydroxy-N-(1-fur-2-ylethyl) urea；N-[1-(2-furyl)ethyl]-N-hydroxyurea；1-[1-(furan-2-yl)ethyl]-1-hydroxyurea
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: YIBAXIRZUZKFMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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：
  79.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基硅基异氰酸酯 以 四氢呋喃 为溶剂， 生成 N-hydroxy-N-(1-fur 2-ylethyl) urea
  参考文献：
  名称：

  Furan and pyrrole containing lipoxygenase inhibiting compounds

  摘要：

  替代呋喃和吡咯化合物可用于抑制脂氧合酶酶，特别是5-脂氧合酶。

  公开号：

  US05112848A1

文献信息

• ACID-CATALYZED ADDITION OF<i>N</i>-HYDROXYUREA TO 1-ARYL ALCOHOL DERIVATIVES: A NEW SYNTHESIS OF ZILEUTON
  作者：Richard R. Copp、Brian T. Fohey、Gregory Lannoye

  DOI：10.1081/scc-100105880

  日期：2001.1

  A highly efficient synthesis of Zileuton is described in which the key step involves a site-specific alkylation of hydroxyurea under acid catalysis. Various aryl alcohol electrophiles were tested and the reaction was found to be highly substrate-specific, favoring benzothiophene and benzofuran-based alcohols.

  描述了齐留通的高效合成，其中关键步骤涉及在酸催化下羟基脲的位点特异性烷基化。测试了各种芳醇亲电试剂，发现该反应具有高度的底物特异性，有利于苯并噻吩和苯并呋喃基醇。
• Structure−Activity Relationships of <i>N</i>-Hydroxyurea 5-Lipoxygenase Inhibitors
  作者：Andrew O. Stewart、Pramila A. Bhatia、Jonathan G. Martin、James B. Summers、Karen E. Rodriques、Michael B. Martin、James H. Holms、Jimmie L. Moore、Richard A. Craig、Teodozyj Kolasa、James D. Ratajczyk、Hormoz Mazdiyasni、Francis A. J. Kerdesky、Shari L. DeNinno、Robert G. Maki、Jennifer B. Bouska、Patrick R. Young、Carmine Lanni、Randy L. Bell、George W. Carter、Clint D. W. Brooks

  DOI：10.1021/jm9700474

  日期：1997.6.1

  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.
• 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
• Ku Yi-Yin, Patel Ramesh R., Roden Brian A., Sawick David P., Tetrahedron Lett., 35 (1994) N 33, S 6017-6020
  作者：Ku Yi-Yin, Patel Ramesh R., Roden Brian A., Sawick David P.

  DOI：——

  日期：——
• FURAN AND PYRROLE CONTAINING LIPOXYGENASE INHIBITING COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP0388429A1

  公开（公告）日：1990-09-26