[1-(3-cyanobenzyl)-2-oxopiperidin-3-(S)-yl]carbamic acid tert butyl ester | 186550-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [1-(3-cyanobenzyl)-2-oxopiperidin-3-(S)-yl]carbamic acid tert butyl ester
• 英文别名: tert-butyl N-[(3S)-1-[(3-cyanophenyl)methyl]-2-oxopiperidin-3-yl]carbamate
• CAS: 186550-60-7
• 化学式: C₁₈H₂₃N₃O₃
• 分子量: 329.399
• InChiKey: FGDYQCIUUXCAMO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(3-cyanobenzyl)-2-oxopiperidin-3-(S)-yl]carbamic acid tert butyl ester 在 盐酸 、 氨 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 3-[(S)-3-(Naphthalene-2-sulfonylamino)-2-oxo-piperidin-1-ylmethyl]-benzamidine
  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：

  3-氰基苯甲醛 在 sodium cyanoborohydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 potassium hydrogencarbonate 、 zinc(II) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 [1-(3-cyanobenzyl)-2-oxopiperidin-3-(S)-yl]carbamic acid tert butyl ester
  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

文献信息

• Design and Structure−Activity Relationships of Potent and Selective Inhibitors of Blood Coagulation Factor Xa
  作者：William R. Ewing、Michael R. Becker、Vincent E. Manetta、Roderick S. Davis、Henry W. Pauls、Helen Mason、Yong Mi Choi-Sledeski、Daniel Green、Don Cha、Alfred P. Spada、Daniel L. Cheney、Jonathan S. Mason、Sebastien Maignan、Jean-Pierre Guilloteau、Karen Brown、Dennis Colussi、Ross Bentley、Jeff Bostwick、Charles J. Kasiewski、Suzanne R. Morgan、Robert J. Leadley、Christopher T. Dunwiddie、Mark H. Perrone、Valeria Chu

  DOI：10.1021/jm990040h

  日期：1999.9.1

  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.