2-adamantan-1-yl-N-[3-(3-morpholin-4-yl-propoxy)cyclohexyl]acetamide | 1061377-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-adamantan-1-yl-N-[3-(3-morpholin-4-yl-propoxy)cyclohexyl]acetamide
• 英文别名: 2-Adamantan-1-yl-N-[3-(3-morpholin-4-yl-propoxy)-cyclohexyl]-acetamide；2-(1-adamantyl)-N-[3-(3-morpholin-4-ylpropoxy)cyclohexyl]acetamide
• CAS: 1061377-78-3
• 化学式: C₂₅H₄₂N₂O₃
• 分子量: 418.62
• InChiKey: YPUVSUVAEBMZCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-adamantan-1-yl-N-(3-hydroxycyclohexyl)acetamide 、 4-(3-溴丙基)吗啉 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-adamantan-1-yl-N-[3-(3-morpholin-4-yl-propoxy)cyclohexyl]acetamide
  参考文献：
  名称：

  Unsymmetrical non-adamantyl N,N′-diaryl urea and amide inhibitors of soluble expoxide hydrolase

  摘要：

  Incorporation of an adamantyl group in prototypical soluble expoxide hydrolase (sEH) inhibitors afforded improved enzyme potency. We explored replacement of the adamantyl group in unsymmetrical ureas and amides with substituted aryl rings to identify equipotent and metabolically stable sEH inhibitors. We found that aryl rings, especially those substituted in the para position with a strongly electron withdrawing substituent, afforded enzyme IC50 values comparable to the adamantyl compounds in an ether substituted, unsymmetrical N,N'-diaryl urea or amide scaffold. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.102

文献信息

• SOLUBLE EPOXIDE HYDROLASE INHIBITORS
  申请人：Gless, JR. Richard D.

  公开号：US20090023731A1

  公开（公告）日：2009-01-22

  Disclosed are urea and thiourea compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, and diabetic-related diseases.

  本发明涉及一种抑制可溶性环氧水解酶（sEH）的尿素和硫脲化合物及其组合物和组合物的制备方法，以及使用这些化合物和组合物治疗患者的方法。这些化合物、组合物和方法对于治疗各种sEH介导的疾病，包括高血压、心血管、炎症和糖尿病相关疾病非常有用。
• [EN] SOLUBLE EPOXIDE HYDROLASE INHIBITORS<br/>[FR] INHIBITEURS D'ÉPOXYDE HYDROLASE SOLUBLE
  申请人：ARETE THERAPEUTICS INC

  公开号：WO2008116145A2

  公开（公告）日：2008-09-25

  [EN] Disclosed are urea and thiourea compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, and diabetic-related diseases.
  [FR] L'invention concerne des composés d'urée et de thiourée et des compositions qui inhibent l'époxyde hydrolase soluble (sEH), des procédés de préparation des composés et des compositions et des procédés de traitement de patients avec de tels composés et de telles compositions. Les composés, compositions et procédés sont utiles pour traiter une variété de maladies induites par sEH, notamment les maladies de l'hypertension, cardiovasculaires, inflammatoires et liées au diabète.
• Unsymmetrical non-adamantyl N,N′-diaryl urea and amide inhibitors of soluble expoxide hydrolase
  作者：Sampath-Kumar Anandan、Heather K. Webb、Zung N. Do、Richard D. Gless

  DOI：10.1016/j.bmcl.2009.05.102

  日期：2009.8

  Incorporation of an adamantyl group in prototypical soluble expoxide hydrolase (sEH) inhibitors afforded improved enzyme potency. We explored replacement of the adamantyl group in unsymmetrical ureas and amides with substituted aryl rings to identify equipotent and metabolically stable sEH inhibitors. We found that aryl rings, especially those substituted in the para position with a strongly electron withdrawing substituent, afforded enzyme IC50 values comparable to the adamantyl compounds in an ether substituted, unsymmetrical N,N'-diaryl urea or amide scaffold. (C) 2009 Elsevier Ltd. All rights reserved.