N-cyclopentylmethyl-N-hydroxyurea

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-cyclopentylmethyl-N-hydroxyurea
• 英文别名: N-(cyclopentylmethyl)-N-hydroxyurea；1-(cyclopentylmethyl)-1-hydroxyurea
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: NSDMWJURYZWZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环戊基甲醇 生成 N-cyclopentylmethyl-N-hydroxyurea
  参考文献：
  名称：

  Cycloalkyl N-hydroxy derivatives having lipoxygenase inhibitory activity

  摘要：

  化合物的结构为##STR1##，其中M是氢、药学上可接受的阳离子或代谢可裂解基团，R是烷基、环烷基或NR.sup.1 R.sup.2，其中R.sup.1和R.sup.2是氢、烷基、环烷基烯酰基或碳环芳基，Y是烷基、烯基或环丙基，A是可选择地取代的环烷基或环烷基烯基，是脂氧合酶酶的有效抑制剂，从而抑制白三烯的生物合成。这些化合物在治疗或改善过敏和炎症性疾病状态方面非常有用。

  公开号：

  US05326787A1

文献信息

• 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.
• US5326787A
  申请人：——

  公开号：US5326787A

  公开（公告）日：1994-07-05
• Cycloalkyl N-hydroxy derivatives having lipoxygenase inhibitory activity
  申请人：Abbott Laboratories

  公开号：US05326787A1

  公开（公告）日：1994-07-05

  Compounds of the structure ##STR1## where M is hydrogen, a pharmaceutically acceptable cation or metabolically cleavable group, R is alkyl, cycloalkyl, or NR.sup.1 R.sup.2, where R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl alkonyl, or carbocyclic aryl, Y is alkylene, alkenylene, or cyclopropyl, and A is optionally substituted cycloalkyl or cycloalkylene are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states.

  化合物的结构为##STR1##，其中M是氢、药学上可接受的阳离子或代谢可裂解基团，R是烷基、环烷基或NR.sup.1 R.sup.2，其中R.sup.1和R.sup.2是氢、烷基、环烷基烯酰基或碳环芳基，Y是烷基、烯基或环丙基，A是可选择地取代的环烷基或环烷基烯基，是脂氧合酶酶的有效抑制剂，从而抑制白三烯的生物合成。这些化合物在治疗或改善过敏和炎症性疾病状态方面非常有用。