N-(1-adamantyl)-5-(4-pentyloxyphenyl)isoxazole-3-carboxamide | 1450606-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(1-adamantyl)-5-(4-pentyloxyphenyl)isoxazole-3-carboxamide
• 英文别名: N-adamantyl-5-(4-(pentyloxy)phenyl)isoxazole-3-carboxamide；N-(1-adamantyl)-5-(4-pentoxyphenyl)-1,2-oxazole-3-carboxamide
• CAS: 1450606-99-1
• 化学式: C₂₅H₃₂N₂O₃
• 分子量: 408.541
• InChiKey: RVXQNANFCJHVPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[4-(戊基氧基)苯基]乙酮 在 盐酸羟胺 、 sodium ethanolate 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 52.75h， 生成 N-(1-adamantyl)-5-(4-pentyloxyphenyl)isoxazole-3-carboxamide
  参考文献：
  名称：

  3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis

  摘要：

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.010

文献信息

• Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines
  作者：Xiao-Wei Zhang、Xiao-Lin He、Nan Yan、Hong-Xing Zheng、Xiang-Guo Hu

  DOI：10.1021/acs.joc.0c02281

  日期：2020.12.4

  A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes leading to isoxazoles or isoxazolines is described. The unprecedented strategy of the oxidation of an amine directly to a nitrile oxide was used in this cyclization process. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerant of a variety of functional

  描述了可商购的胺和亚硝酸叔丁酯与炔或烯烃的容易的氧化性杂环化，其导致异恶唑或异恶唑啉。在这种环化过程中使用了前所未有的将胺直接氧化为一氧化氮的策略。该反应是高效的，区域特异性的，操作简单的，温和的，并且耐受多种官能团。对照实验为这种新型的氧化环化反应提供了一种一氧化氮中间体机制。此外，实现了对生物活性分子骨架的合成应用和药物的后期修饰。
• 3-Carboxamido-5-aryl-isoxazoles as new CB2 agonists for the treatment of colitis
  作者：Aurélien Tourteau、Virginie Andrzejak、Mathilde Body-Malapel、Lucas Lemaire、Amélie Lemoine、Roxane Mansouri、Madjid Djouina、Nicolas Renault、Jamal El Bakali、Pierre Desreumaux、Giulio G. Muccioli、Didier M. Lambert、Philippe Chavatte、Benoît Rigo、Natascha Leleu-Chavain、Régis Millet

  DOI：10.1016/j.bmc.2013.06.010

  日期：2013.9

  Recent investigations showed that anandamide, the main endogenous ligand of CB1 and CB2 cannabinoid receptors, possesses analgesic, antidepressant and anti-inflammatory effects. In the perspective to treat inflammatory bowel disease (IBD), our approach was to develop new selective CB2 receptor agonists without psychotropic side effects associated to CB1 receptors. In this purpose, a new series of 3-carboxamido-5-aryl-isoxazoles, never described previously as CB2 receptor agonists, was designed, synthesized and evaluated for their biological activity. The pharmacological results have identified great selective CB2 agonists with in vivo anti-inflammatory activity in a DSS-induced acute colitis mouse model. (C) 2013 Elsevier Ltd. All rights reserved.