N-cyclohexyl-N'-[2]naphthyl-urea | 109245-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-cyclohexyl-N'-[2]naphthyl-urea
• 英文别名: N-Cyclohexyl-N'-[2]naphthyl-harnstoff；1-Cyclohexyl-3--harnstoff；1-Cyclohexyl-3-naphthalen-2-yl-urea；1-cyclohexyl-3-naphthalen-2-ylurea
• CAS: 109245-35-4
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: AAOGJTCYBSSQBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N¹-(2-Naphthyl)-biguanid 在 盐酸 作用下， 生成 N-cyclohexyl-N'-[2]naphthyl-urea
  参考文献：
  名称：

  Urbanski et al., Roczniki Chemii, 1959, vol. 33, p. 1383,1387

  摘要：

  DOI：

文献信息

• Design, Synthesis, and Structure−Activity Relationships of Alkylcarbamic Acid Aryl Esters, a New Class of Fatty Acid Amide Hydrolase Inhibitors
  作者：Giorgio Tarzia、Andrea Duranti、Andrea Tontini、Giovanni Piersanti、Marco Mor、Silvia Rivara、Pier Vincenzo Plazzi、Chris Park、Satish Kathuria、Daniele Piomelli

  DOI：10.1021/jm021119g

  日期：2003.6.1

  Fatty acid amide hydrolase (FAAH), an intracellular serine hydrolase enzyme, participates in the deactivation of fatty acid ethanolamides such as the endogenous cannabinoid anandamide, the intestinal satiety factor oleoylethanolamide, and the peripheral analgesic and anti-inflammatory factor palmitoylethanolamide. In the present study, we report on the design, synthesis, and structure-activity relationships

  脂肪酸酰胺水解酶（FAAH）是一种细胞内丝氨酸水解酶，参与脂肪酸乙醇酰胺的失活，例如内源性大麻素大麻素，肠饱足性因子油酰基乙醇酰胺以及外周镇痛和抗炎因子棕榈酰乙醇酰胺。在本研究中，我们报告了一类新型的，有效的，选择性的和系统活性的FAAH活性抑制剂的设计，合成和构效关系（SAR），我们最近证明它们具有有效的抗焦虑作用在大鼠中。这些化合物的特征在于氨基甲酸酯模板在其O-和N-末端被烷基或芳基取代。大多数化合物抑制FAAH，但不能抑制其他几种丝氨酸水解酶，其效力取决于取代基的大小和形状。最初的SAR研究表明，最佳效能的要求是亲脂性N-烷基取代基（例如正丁基或环己基）和弯曲的O-芳基取代基。此外，氨基甲酸酯基对于活性是必不可少的。对烷基氨基甲酸芳基酯的3D-QSAR分析表明，O-芳基部分的大小和形状与FAAH抑制能力有关。构建了CoMSIA模型，表明与O-苯基环的间位置相对应的区域的空间占据可提
• Modulation of anxiety through blockade of anandamide hydrolysis
  申请人：Piomelli Daniele

  公开号：US20090048337A1

  公开（公告）日：2009-02-19

  Fatty acid amide hydrolase inhibitors of the Formula: I. are provided wherein X is NH, CH 2 , O, or S; Q is O or S; Z is O or N; R is an aromatic moiety selected from the group consisting of substituted or unsubstituted aryl; substituted or unsubstituted biphenylyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenyl; substituted or unsubstituted terphenylyl; substituted or unsubstituted cycloalkyl, heteroaryl, or alkyl; and R 1 and R 2 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, and substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; with the proviso that if Z is O, one of R 1 and R 2 is absent, and that if Z is N, optionally R 1 and R 2 may optionally be taken together to form a substituted or unsubstituted N-heterocycle or substituted or unsubstituted heteroaryl with the N atom to which they are each attached. Pharmaceutical compositions comprising the compounds of Formula I and methods of using them to inhibit FAAH and/or treat appetite disorders, glaucoma, pain, insomnia, and neurological and psychological disorders including anxiety disorders, epilepsy, and depression are provided.

  提供了公式为I的脂肪酸酰胺水解酶抑制剂，其中X为NH，CH2，O或S; Q为O或S; Z为O或N; R为从取代或未取代芳基; 取代或未取代的联苯基; 取代或未取代的萘基; 取代或未取代的苯基; 取代或未取代的三苯基基; 取代或未取代的环烷基，杂环芳基或烷基中选择的芳香基；R1和R2独立地选择自H，取代或未取代的烷基，取代或未取代的杂环烷基，取代或未取代的苯基，取代或未取代的联苯基，取代或未取代的芳基，取代或未取代的杂环芳基的群体中；但如果Z为O，则R1和R2中的一个不存在，如果Z为N，则可选地将R1和R2结合在一起形成取代或未取代的N-杂环或取代或未取代的杂环芳基，与它们各自连接的N原子。提供了包含公式I化合物的药物组合物以及使用它们抑制FAAH和/或治疗食欲障碍，青光眼，疼痛，失眠以及神经和心理障碍，包括焦虑症，癫痫和抑郁症的方法。
• INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Dasse Olivier

  公开号：US20070155747A1

  公开（公告）日：2007-07-05

  Pharmacological inhibition of fatty acid amide hydrolase (FAAH) activity leads to increased levels of fatty acid amides. Esters of alkylcarbamic acids are disclosed that are inhibitors of FAAH activity. Compounds disclosed herein inhibit FAAH activity. Described herein are processes for the preparation of esters of alkylcarbamic acid compounds, compositions that include them, and methods of use thereof.

  药物抑制脂肪酸酰胺水解酶（FAAH）活性会导致脂肪酸酰胺水平的增加。本文披露了烷基氨基酸酯类化合物，其可作为FAAH活性抑制剂。本文披露的化合物可抑制FAAH活性。本文还描述了制备烷基氨基酸酯类化合物的方法、包括它们的组合物以及使用它们的方法。
• MODULATION OF ANXIETY THROUGH BLOCKADE OF ANANDAMIDE HYDROLYSIS
  申请人：Piomelli Daniele

  公开号：US20120010283A1

  公开（公告）日：2012-01-12

  Fatty acid amide hydrolase inhibitors of the Formula: are provided wherein X is NH, CH 2 , O, or S; Q is O or S; Z is O or N; R is an aromatic moiety selected from the group consisting of substituted or unsubstituted aryl; substituted or unsubstituted biphenylyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenyl; substituted or unsubstituted terphenylyl; substituted or unsubstituted cycloalkyl, heteroaryl, or alkyl; and R 1 and R 2 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, and substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; with the proviso that if Z is O, one of R 1 and R 2 is absent, and that if Z is N, optionally R 1 and R 2 may optionally be taken together to form a substituted or unsubstituted N-heterocycle or substituted or unsubstituted heteroaryl with the N atom to which they are each attached. Pharmaceutical compositions comprising the compounds of Formula I and methods of using them to inhibit FAAH and/or treat appetite disorders, glaucoma, pain, insomnia, and neurological and psychological disorders including anxiety disorders, epilepsy, and depression are provided.

  提供了公式为的脂肪酸酰胺水解酶抑制剂：其中X为NH，CH2，O或S；Q为O或S；Z为O或N；R为从取代或未取代芳基；取代或未取代联苯基；取代或未取代萘基；取代或未取代苯基；取代或未取代三苯基基；取代或未取代环烷基，杂环芳基或烷基中选择的芳香基；R1和R2分别选择自H，取代或未取代烷基，取代或未取代杂环烷基，取代或未取代苯基，取代或未取代联苯基，取代或未取代芳基和取代或未取代杂环芳基的群中；但是如果Z为O，则R1和R2中的一个不存在，如果Z为N，则可选地将R1和R2结合在一起形成取代或未取代的N-杂环或取代或未取代的杂环芳基，与它们各自连接的N原子。提供了包含公式I化合物的制药组合物以及使用它们来抑制FAAH和/或治疗食欲障碍，青光眼，疼痛，失眠以及神经和心理障碍，包括焦虑症，癫痫和抑郁症的方法。
• Inhibitors for the Soluble Epoxide Hydrolase
  申请人：HAMMOCK BRUCE D.

  公开号：US20110021448A1

  公开（公告）日：2011-01-27

  Inhibitors of the soluble epoxide hydrolase (sEH) are provided that incorporate multiple pharmacophores and are useful in the treatment of diseases.

  提供了可用于治疗疾病的可溶性环氧酶（sEH）抑制剂，其中包含多个药效团。