3-(4-cyanobenzyloxy)-5-isoxazolecarboxylic acid | 169605-38-3

• 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-cyanobenzyloxy)-5-isoxazolecarboxylic acid
• 英文别名: 3-[(4-Cyanophenyl)methoxy]-1,2-oxazole-5-carboxylic acid
• CAS: 169605-38-3
• 化学式: C₁₂H₈N₂O₄
• 分子量: 244.207
• InChiKey: DUZAGFVCYYBHIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-cyanobenzyloxy)-5-isoxazolecarboxylic acid 在 盐酸 、 lithium hydroxide 、 碳酸氢铵 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-(butoxycarbonylamino)-3-[[3-[(4-carbamimidoylphenyl)methoxy]-1,2-oxazole-5-carbonyl]amino]propanoic acid;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists

  摘要：

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00637-4
• 作为产物：
  描述：

  对氰基溴化苄 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(4-cyanobenzyloxy)-5-isoxazolecarboxylic acid
  参考文献：
  名称：

  Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists

  摘要：

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00637-4

文献信息

• [EN] COMPOUNDS CONTAINING BASIC AND ACIDIC TERMINI USEFUL AS FIBRINOGEN RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES CONTENANT DES TERMINAISONS BASIQUES ET ACIDES UTILES EN TANT QU'ANTAGONISTES DES RECEPTEURS DE FIBRINOGENE
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1995018111A1

  公开（公告）日：1995-07-06

  (EN) This invention relates to novel compounds containing basic and acidic termini, pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.(FR) Nouveaux composés contenant des terminaisons basiques et acides, compositions pharmaceutiques contenant lesdits composés, procédés pour préparer lesdits composés et procédés d'utilisation desdits composés, seuls ou en combinaison avec d'autres agents thérapeutiques, afin d'inhiber l'agrégation plaquettaire, afin de servir d'agents thrombolytiques, et/ou afin de traiter des troubles thromboemboliques.

  该发明涉及新型化合物，其含有碱性和酸性末端，含有这种化合物的制药组合物，制备这种化合物的方法，以及使用这些化合物的方法，单独或与其他治疗剂联合使用，用于抑制血小板聚集，作为溶栓剂以及治疗血栓栓塞性疾病。
• US5563158A
  申请人：——

  公开号：US5563158A

  公开（公告）日：1996-10-08
• US5691329A
  申请人：——

  公开号：US5691329A

  公开（公告）日：1997-11-25
• Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists
  作者：Chu-Biao Xue、John Roderick、Shaker Mousa、Richard E. Olson、William F. DeGrado

  DOI：10.1016/s0960-894x(98)00637-4

  日期：1998.12

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.