1-benzyl-3-hexanoylurea | 28615-01-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 1-benzyl-3-hexanoylurea
• 英文别名: N-Benzyl-N'-caproyl-harnstoff
• CAS: 28615-01-2
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: BRJLWSAPRNMJJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  己酸酐 、 苄脲 以 甲苯 为溶剂， 反应 33.0h， 以61%的产率得到1-benzyl-3-hexanoylurea
  参考文献：
  名称：

  Evaluation of anticonvulsant and analgesic effects of benzyl- and benzhydryl ureides

  摘要：

  The anticonvulsant effects of benzyl- and benzhydryl ureides in mice models of seizures (maximal electroshock seizure test, pentylenetetrazol test, picrotoxin-induced seizure test) and the influence on spontaneous locomotor activity has been assessed. Furthermore, the analgesic effect of ureide derivatives was studied in the hot-plate test in mice. Selected compounds were investigated for their in vitro interaction with adenosine receptors as well as the benzodiazepine binding site of GABA(A) receptors. This study demonstrated the strong anticonvulsant activity of several ureides in electrically or chemically induced seizure models, and structure-activity relationships were discussed. 1-Benzyl-3-butyrylurea (9) was found to be equipotent to ethosuximide in the pentylenetetrazol test with regard to the number of attacks as well as the time of the onset of seizures. The ureide 9 also revealed the highest protective activity against seizures in the other models, maximal electroshock seizure and picrotoxin test. Moreover, 1-benzyl-3-butyrylurea was not neurotoxic at doses up to 200 mg/kg. Benzylureides 8-10 showed affinity to the adenosine A, receptors at low micromolar concentrations. However, the apparent anticonvulsant activity in different seizure models does not appear to result from direct activation of adenosine A, receptors or GABAA receptors, respectively. In the hot-plate test, the majority of investigated compounds exhibited analgesic activity. Again, compound 9 was superior to the other substances investigated, suggesting a potential therapeutic value of that ureide derivative. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2006.12.002