1-(2-octyloxyphenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-octyloxyphenyl)ethanone
• 英文别名: 1-(2-Octoxyphenyl)ethanone
• 化学式: C₁₆H₂₄O₂
• mdl: MFCD11542574
• 分子量: 248.365
• InChiKey: DWNLXMIRIOTUCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-octyloxyphenyl)ethanone 在 盐酸羟胺 、 sodium ethanolate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 5-(2-octyloxyphenyl)isoxazole-3-carboxylic acid
  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
• 作为产物：
  描述：

  1-溴辛烷 、 2'-羟基苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以69%的产率得到1-(2-octyloxyphenyl)ethanone
  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

• Gionis; Fugnitto; Strzelecka, Molecular Crystals and Liquid Crystals (1969-1991), 1983, vol. 95, # 3-4, p. 351 - 358
  作者：Gionis、Fugnitto、Strzelecka、Le Barny

  DOI：——

  日期：——
• Synthese et Proprietes Redox des π-Donneurs Mesogenes
  作者：V. Gionis、R. Fugnitto、G. Meyer、H. Strzelecka、J. C. Dubois

  DOI：10.1080/00268948208076178

  日期：1982.11
• 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.