[Naphthalen-1-ylmethyl-(3-phenylisoxazol-5-yl)-amino]-acetic acid ethyl ester | 359424-59-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [Naphthalen-1-ylmethyl-(3-phenylisoxazol-5-yl)-amino]-acetic acid ethyl ester
• 英文别名: [Naphthalen-1-ylmethyl-(3-phenyl-isoxazol-5-yl)-amino]-acetic acid ethyl ester；ethyl 2-[naphthalen-1-ylmethyl-(3-phenyl-1,2-oxazol-5-yl)amino]acetate
• CAS: 359424-59-2
• 化学式: C₂₄H₂₂N₂O₃
• 分子量: 386.45
• InChiKey: PJQFFZBTLJFCEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [Naphthalen-1-ylmethyl-(3-phenylisoxazol-5-yl)-amino]-acetic acid ethyl ester 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid 2-[naphthalen-1-ylmethyl-(3phenylisoxazol-5-yl)-amino]ethyl ester
  参考文献：
  名称：

  Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)

  摘要：

  The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50S of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00745-4
• 作为产物：
  描述：

  溴乙酸乙酯 、 naphthalen-1-ylmethyl-(3-phenyl-isoxazol-5-yl)amine 以 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 以73.9%的产率得到[Naphthalen-1-ylmethyl-(3-phenylisoxazol-5-yl)-amino]-acetic acid ethyl ester
  参考文献：
  名称：

  Thrombin receptor antagonists

  摘要：

  一种具有以下公式的凝血酶受体拮抗剂，用于抑制血小板聚集。这些化合物可用于作用于凝血酶受体的方法，包括向哺乳动物，最好是人类，投与治疗有效但非毒性量的该化合物。

  公开号：

  US06544982B1

文献信息

• Thrombin receptor antagonists
  申请人：Merck & Co., Inc.

  公开号：US06544982B1

  公开（公告）日：2003-04-08

  A thrombin receptor antagonist having the formula useful for inhibiting the aggregation of blood platelets. The compounds can be used in a method of acting upon a thrombin receptor which comprises administering a therapeutically effective but non-toxic amount of such compound to a mammal, preferably a human.

  一种具有以下公式的凝血酶受体拮抗剂，用于抑制血小板聚集。这些化合物可用于作用于凝血酶受体的方法，包括向哺乳动物，最好是人类，投与治疗有效但非毒性量的该化合物。
• US6544982B1
  申请人：——

  公开号：US6544982B1

  公开（公告）日：2003-04-08
• Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)
  作者：Philippe G Nantermet、James C Barrow、George F Lundell、Janetta M Pellicore、Kenneth E Rittle、MaryBeth Young、Roger M Freidinger、Thomas M Connolly、Cindra Condra、Jerzy Karczewski、Rodney A Bednar、Stanley L Gaul、Robert J Gould、Kris Prendergast、Harold G Selnick

  DOI：10.1016/s0960-894x(01)00745-4

  日期：2002.2

  The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50S of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min. (C) 2002 Published by Elsevier Science Ltd.