ethyl 5-(1,1'-biphenyl-3-yl)-isoxazole-3-carboxylate | 1314023-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(1,1'-biphenyl-3-yl)-isoxazole-3-carboxylate
• 英文别名: ethyl 5-(3-phenylphenyl)isoxazole-3-carboxylate；Ethyl 5-(3-Biphenylyl)isoxazole-3-carboxylate；ethyl 5-(3-phenylphenyl)-1,2-oxazole-3-carboxylate
• CAS: 1314023-84-1
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: AASWMFIQQSOOCI-UHFFFAOYSA-N

物化性质

• 沸点：
  480.4±33.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-(1,1'-biphenyl-3-yl)-isoxazole-3-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以75%的产率得到5-(1,1'-biphenyl-3-yl)-isoxazole-3-carboxylic acid
  参考文献：
  名称：

  New FAAH inhibitors based on 3-carboxamido-5-aryl-isoxazole scaffold that protect against experimental colitis

  摘要：

  Growing evidence suggests a role for the endocannabinoid (EC) system, in intestinal inflammation and compounds inhibiting anandamide degradation offer a promising therapeutic option for the treatment of inflammatory bowel diseases. In this paper, we report the first series of carboxamides derivatives possessing FAAH inhibitory activities. Among them, compound 39 displayed significant inhibitory FAAH activity (IC50 = 0.088 mu M) and reduced colitis induced by intrarectal administration of TNBS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.057
• 作为产物：
  描述：

  3-乙酰基联苯 在 盐酸羟胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 ethyl 5-(1,1'-biphenyl-3-yl)-isoxazole-3-carboxylate
  参考文献：
  名称：

  New FAAH inhibitors based on 3-carboxamido-5-aryl-isoxazole scaffold that protect against experimental colitis

  摘要：

  Growing evidence suggests a role for the endocannabinoid (EC) system, in intestinal inflammation and compounds inhibiting anandamide degradation offer a promising therapeutic option for the treatment of inflammatory bowel diseases. In this paper, we report the first series of carboxamides derivatives possessing FAAH inhibitory activities. Among them, compound 39 displayed significant inhibitory FAAH activity (IC50 = 0.088 mu M) and reduced colitis induced by intrarectal administration of TNBS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.057

文献信息

• Synthesis of Ethyl Isoxazole-3-Carboxylates Using an Ionic Liquid as a Soluble Support
  作者：Shouri Sheng、Wusheng Sheng、Qiaosheng Hu、Hongen Qu、Mingzhong Cai

  DOI：10.1002/jhet.1673

  日期：2014.3

  3‐dipolar cycloadditions of ionic liquid‐supported vinyl ethers, derived from ionic liquid‐supported α‐phenylselenomethyl ether, with ethyl cyanoformate N‐oxide gave supported isoxazoline derivatives, which were then cleaved from the ionic liquid support under mild acidic conditions to afford ethyl isoxazole‐3‐carboxylates. This new synthetic method is simple and efficient and the products are obtained

  离子液体负载的乙烯基醚的区域选择性1,3-偶极环加成反应，由离子液体负载的α-苯基硒代甲基醚与氰基甲酸乙酯N-氧化物形成，得到负载的异恶唑啉衍生物，然后在温和的酸性条件下从离子液体载体上裂解下来。提供异恶唑-3-羧酸乙酯的条件。这种新的合成方法简单有效，可以高收率获得产品。
• New FAAH inhibitors based on 3-carboxamido-5-aryl-isoxazole scaffold that protect against experimental colitis
  作者：Virginie Andrzejak、Giulio G. Muccioli、Mathilde Body-Malapel、Jamal El Bakali、Madjid Djouina、Nicolas Renault、Philippe Chavatte、Pierre Desreumaux、Didier M. Lambert、Régis Millet

  DOI：10.1016/j.bmc.2011.04.057

  日期：2011.6

  Growing evidence suggests a role for the endocannabinoid (EC) system, in intestinal inflammation and compounds inhibiting anandamide degradation offer a promising therapeutic option for the treatment of inflammatory bowel diseases. In this paper, we report the first series of carboxamides derivatives possessing FAAH inhibitory activities. Among them, compound 39 displayed significant inhibitory FAAH activity (IC50 = 0.088 mu M) and reduced colitis induced by intrarectal administration of TNBS. (C) 2011 Elsevier Ltd. All rights reserved.