3,4-diphenyl-5-ethylisoxazole | 74048-23-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 3,4-diphenyl-5-ethylisoxazole
• 英文别名: 5-ethyl-3,4-diphenyl-isoxazole；5-ethyl-3,4-diphenyl-1,2-oxazole
• CAS: 74048-23-0
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: MXTWADCRLRQMDW-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C(Solv: hexane (110-54-3))
• 沸点：
  376.0±31.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  帕瑞昔布中间体 在 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 3,4-diphenyl-5-ethylisoxazole
  参考文献：
  名称：

  Novel Synthesis of 3,4-Diarylisoxazole Analogues of Valdecoxib:  Reversal Cyclooxygenase-2 Selectivity by Sulfonamide Group Removal

  摘要：

  3,4-Diarylisoxazole analogues of valdecoxib [4-(5-methyl-3-phenylisoxazol-4-yl)-benzensulfonamide], a selective cyclooxygenase-2 (COX-2) inhibitor, were synthesized by 1,3-dipolar cycloaddition of arylnitrile oxides to the enolate ion of phenylacetone regioselectively prepared in situ with lithium diisopropylamide at 0 degreesC. The corresponding 3-aryl-5-methyl-4-phenylisoxazoles were easily generated by a dehydration/aromatization reaction under basic conditions of 3-aryl-5-hydroxy-5-methyl-4-phenyl-2-isoxazolines and further transformed into their benzenesulfonamide derivatives. The biochemical COX-1/COX-2 selectivity was evaluated in vitro by using the human whole blood assays of COX isozyme activity. Three compounds not bearing the sulfonamide group present in valdecoxib were selective COX-1 inhibitors.

  DOI：

  10.1021/jm040782x

文献信息

• Functionalized diarylisoxazoles inhibitors of ciclooxygenase
  申请人：Scilimati Antonio

  公开号：US20090181970A1

  公开（公告）日：2009-07-16

  The present invention refers to isoxazole derivatives, in particular diarylisoxazole derivatives inhibitors of cyclooxygenase (COX), in particular cyclooxygenase-1 (COX-1), to their pharmaceutical compositions, the process for their preparation and their use for the chemoprevention and treatment of inflammatory syndromes and in the prevention and treatment of carcinomas, in particular intestinal, ovarian and cutaneous carcinomas, in the treatment of pain syndromes, in particular after surgery, and in the cardiovascular field as antithrombotics/vasoprotectives/cardioprotectives.

  本发明涉及异恶唑衍生物，特别是二芳基异恶唑衍生物，用作环氧合酶（COX）的抑制剂，特别是环氧合酶-1（COX-1）的抑制剂，以及它们的药物组合物、其制备方法以及用于化学预防和治疗炎症综合征以及预防和治疗癌症，特别是肠癌、卵巢癌和皮肤癌，在疼痛综合征的治疗中，特别是手术后，以及在心血管领域作为抗血栓/血管保护剂/心脏保护剂的用途。
• [EN] METHOD FOR THE PREPARATION OF DIARYLISOXAZOLE SULFONAMIDE COMPOUNDS AND INTERMEDIATES<br/>[FR] PROCEDES DESTINES LA PREPARATION D'UN COMPOSE DE DIARYLISOXAZOLE SULFONAMIDE ET D'INTERMEDIAIRES
  申请人：PHARMACIA CORP

  公开号：WO2005123701A1

  公开（公告）日：2005-12-29

  The disclosure provides a method for the preparation of a diarylisoxazolé sulfonamide compound comprising contacting a deoxybenzoin with a secondary amine to form a diarylenamine compound; contacting the diarylenamine compound with an acetylating agent to form an acetyl diarylenamine compound; contacting the acetyl diarylenamine compound with a source of hydroxylamine to form an diaryl isoxazolol compound; eliminating water from the diaryl isoxazolol compound to form a diaryl isoxazole compound, chlorosulfonating the diarylisoxazole compound to form a chlorosulfonyl diaryl isoxazole compound; and contacting the chlorosulfonyl diaryl isoxazole compound with a source of ammonia to form the diarylisoxazole sulfonamide compound.

  该公开提供了一种制备二芳基异噁唑磺胺化合物的方法，包括将脱氧苯并与二级胺接触以形成二芳胺化合物；将二芳胺化合物与乙酰化剂接触以形成乙酰二芳胺化合物；将乙酰二芳胺化合物与羟胺源接触以形成二芳异噁唑醇化合物；从二芳异噁唑醇化合物中除去水分以形成二芳异噁唑化合物，将二芳异噁唑化合物氯磺化以形成氯磺基二芳异噁唑化合物；并将氯磺基二芳异噁唑化合物与氨源接触以形成二芳异噁唑磺胺化合物。
• Use of isoxazole derivatives as cyclooxygenase inhibitors
  申请人：Universita' degli Studi di Bari

  公开号：EP2246337A1

  公开（公告）日：2010-11-03

  The present invention refers to the use of a compound selected from 3,4-diphenyl-5-ethylisoxazole and 3,4-diphenyl-5-methylisoxazole as inhibitors of cyclooxygenase, in particular of cyclooxygenase 1 and 2 (COX-1) (COX-2).

  本发明涉及一种选自 3,4-二苯基-5-乙基异噁唑和 3,4-二苯基-5-甲基异噁唑的化合物作为环氧化酶，特别是环氧化酶 1 和 2（COX-1）（COX-2）的抑制剂的用途。
• Bellec,C. et al., Journal of Heterocyclic Chemistry, 1979, vol. 16, p. 1657 - 1659
  作者：Bellec,C. et al.

  DOI：——

  日期：——
• [EN] ISOXAZOLE DERIVATIVES AND THEIR USE AS CYCLOOXYGENASE INHIBITORS<br/>[FR] DERIVES ISOXAZOLE ET UTILISATION EN TANT QU'INHIBITEURS DE CYCLOOXYGENASE
  申请人：UNIV BARI

  公开号：WO2005068442A3

  公开（公告）日：2006-04-06