(3S)-3-amino-1-[(1-chloro-6-methoxyisoquinolin-7-yl)methyl]pyrrolidin-2-one | 250645-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (3S)-3-amino-1-[(1-chloro-6-methoxyisoquinolin-7-yl)methyl]pyrrolidin-2-one
• CAS: 250645-12-6
• 化学式: C₁₅H₁₆ClN₃O₂
• 分子量: 305.764
• InChiKey: DWIWPUZZBJNSHM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-amino-1-[(1-chloro-6-methoxyisoquinolin-7-yl)methyl]pyrrolidin-2-one 在 ammonium acetate 、 三乙胺 、 苯酚 作用下， 以 乙腈 为溶剂， 生成 N-[(3S)-1-[(1-amino-6-methoxyisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide
  参考文献：
  名称：

  Aminoisoquinolines: Design and synthesis of an orally active benzamidine isostere for the inhibition of factor XA

  摘要：

  The design, synthesis and SAR of sulfonamidopyrrolidinone, fXa inhibitors incorporating a new benzamidine isostere, namely aminoisoquinolines, is described. These inhibitors have higher Caco-2 cell permeability than comparable benzamidines and attain higher levels of exposure upon oral dosing. The most potent member 14b (fXa Ki=6 nM) is selective against other serine proteases of interest (>600 fold). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00421-7
• 作为产物：
  描述：

  1-氯-6-甲氧基-7-甲基异喹啉 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙酸乙酯 为溶剂， 生成 (3S)-3-amino-1-[(1-chloro-6-methoxyisoquinolin-7-yl)methyl]pyrrolidin-2-one
  参考文献：
  名称：

  Aminoisoquinolines: Design and synthesis of an orally active benzamidine isostere for the inhibition of factor XA

  摘要：

  The design, synthesis and SAR of sulfonamidopyrrolidinone, fXa inhibitors incorporating a new benzamidine isostere, namely aminoisoquinolines, is described. These inhibitors have higher Caco-2 cell permeability than comparable benzamidines and attain higher levels of exposure upon oral dosing. The most potent member 14b (fXa Ki=6 nM) is selective against other serine proteases of interest (>600 fold). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00421-7

文献信息

• SULFONIC ACID OR SULFONYLAMINO N-(HETEROARALKYL)-AZAHETEROCYCLYLAMIDE COMPOUNDS
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP0944386B1

  公开（公告）日：2002-09-18
• US6281227B1
  申请人：——

  公开号：US6281227B1

  公开（公告）日：2001-08-28
• US6602864B1
  申请人：——

  公开号：US6602864B1

  公开（公告）日：2003-08-05
• [EN] SULFONIC ACID OR SULFONYLAMINO N-(HETEROARALKYL)-AZAHETEROCYCLYLAMIDE COMPOUNDS<br/>[FR] COMPOSES A BASE D'ACIDE SULFONIQUE OU DE SULFONYL-AMINO N-(HETEROARALKYL)-AZAHETEROCYCLYLAMIDE
  申请人：AVENTIS PHARMA GMBH

  公开号：WO2001039759A2

  公开（公告）日：2001-06-07

  The compounds of formula (I) herein exhibit useful phamacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula (I), compositions containing compounds of formula (I), and their use, which are for treating a patient suffering from, or subject to, physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.
• Aminoisoquinolines: Design and synthesis of an orally active benzamidine isostere for the inhibition of factor XA
  作者：Y.M. Choi-Sledeski、M.R. Becker、D.M. Green、R. Davis、W.R. Ewing、H.J. Mason、C. Ly、A. Spada、G. Liang、D. Cheney、J. Barton、V. Chu、K. Brown、D. Colussi、R. Bentley、R. Leadley、C. Dunwiddie、H.W. Pauls

  DOI：10.1016/s0960-894x(99)00421-7

  日期：1999.9

  The design, synthesis and SAR of sulfonamidopyrrolidinone, fXa inhibitors incorporating a new benzamidine isostere, namely aminoisoquinolines, is described. These inhibitors have higher Caco-2 cell permeability than comparable benzamidines and attain higher levels of exposure upon oral dosing. The most potent member 14b (fXa Ki=6 nM) is selective against other serine proteases of interest (>600 fold). (C) 1999 Elsevier Science Ltd. All rights reserved.