ethyl 5-([1,1′-biphenyl]-4-yl)isoxazole-3-carboxylate | 109807-20-7

• 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]-4-yl)isoxazole-3-carboxylate
• 英文别名: ethyl 5-biphen-4-yl-isoxazole-3-carboxylate；5-biphenyl-4-yl-isoxazole-3-carboxylic acid ethyl ester；5-Biphenyl-4-yl-isoxazol-3-carbonsaeure-aethylester；Ethyl 5-(4-Biphenylyl)isoxazole-3-carboxylate；ethyl 5-(4-phenylphenyl)-1,2-oxazole-3-carboxylate
• CAS: 109807-20-7
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: DRJUERDDRKPRNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  501.8±38.0 °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]-4-yl)isoxazole-3-carboxylate 在 乙醇 、 硫酸 、 sodium hydroxide 作用下， 生成 (5-biphenyl-4-yl)isoxazole-3-carboxylic acid isopropyl ester
  参考文献：
  名称：

  5-芳基乙烯基和5-（杂）芳基-3-异恶唑羧酸酯的抗结核剂合成与评价

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21057
• 作为产物：
  描述：

  2-hydroxy-4-oxo-4-(4-biphenylyl)but-2-enoic acid ethyl ester 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到ethyl 5-([1,1′-biphenyl]-4-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

• 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。
• Fatutta; Balestra, Gazzetta Chimica Italiana, 1958, vol. 88, p. 899,907
  作者：Fatutta、Balestra

  DOI：——

  日期：——
• Synthesis and Evaluation as Antitubercular Agents of 5-Arylethenyl and 5-(Hetero)aryl-3-Isoxazolecarboxylate
  作者：Claudia Vergelli、Agostino Cilibrizzi、Letizia Crocetti、Alessia Graziano、Vittorio Dal Piaz、Baojie Wan、Yuehong Wang、Scott Franzblau、Maria Paola Giovannoni

  DOI：10.1002/ddr.21057

  日期：2013.5

  Preclinical Research

  临床前研究
• 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.