2-[<1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl>-7-methoxynaphthalen-2-ylsulfonylamino]-N-acetic acid | 186551-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[<1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl>-7-methoxynaphthalen-2-ylsulfonylamino]-N-acetic acid
• 英文别名: 2-[[(3S)-1-[(3-cyanophenyl)methyl]-2-oxopyrrolidin-3-yl]-(7-methoxynaphthalen-2-yl)sulfonylamino]acetic acid
• CAS: 186551-29-1
• 化学式: C₂₅H₂₃N₃O₆S
• 分子量: 493.54
• InChiKey: WTAJEWNLLYZDSF-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[<1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl>-7-methoxynaphthalen-2-ylsulfonylamino]-N-acetic acid 在 盐酸 、 ammonium hydroxide 、 氨 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 46.25h， 生成 2-[[(S)-1-(3-Carbamimidoyl-benzyl)-2-oxo-pyrrolidin-3-yl]-(7-methoxy-naphthalene-2-sulfonyl)-amino]-acetamide
  参考文献：
  名称：

  Design and Structure−Activity Relationships of Potent and Selective Inhibitors of Blood Coagulation Factor Xa

  摘要：

  The discovery of a series of non-peptide factor Xa (FXa) inhibitors incorporating 3-(S)-amino-2-pyrrolidinone as a central template is described. After identifying compound 4, improvements in in vitro potency involved modifications of the liphophilic group and optimizing the angle of presentation of the amidine group to the S1 pocket of FXa. These studies ultimately led to compound RPR120844, a potent inhibitor of FXa (Ki = 7 nM) which shows selectivity for FXa over trypsin, thrombin, and several fibrinolytic serine proteinases. RPR120844 is an effective anticoagulant in both the rat model of FeCl2-induced carotid artery thrombosis and the rabbit model of jugular vein thrombus formation.

  DOI：

  10.1021/jm990040h
• 作为产物：
  描述：

  [1-(3-cyanobenzyl)-2-oxopyrrolidin-3(S)-yl]carbamic acid tert-butyl ester 在 盐酸 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 59.0h， 生成 2-[<1-(3-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl>-7-methoxynaphthalen-2-ylsulfonylamino]-N-acetic acid
  参考文献：
  名称：

  Design and Structure−Activity Relationships of Potent and Selective Inhibitors of Blood Coagulation Factor Xa

  摘要：

  The discovery of a series of non-peptide factor Xa (FXa) inhibitors incorporating 3-(S)-amino-2-pyrrolidinone as a central template is described. After identifying compound 4, improvements in in vitro potency involved modifications of the liphophilic group and optimizing the angle of presentation of the amidine group to the S1 pocket of FXa. These studies ultimately led to compound RPR120844, a potent inhibitor of FXa (Ki = 7 nM) which shows selectivity for FXa over trypsin, thrombin, and several fibrinolytic serine proteinases. RPR120844 is an effective anticoagulant in both the rat model of FeCl2-induced carotid artery thrombosis and the rabbit model of jugular vein thrombus formation.

  DOI：

  10.1021/jm990040h