Ethyl 4-(benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-4-oxobutanoate | 1026018-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: Ethyl 4-(benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-4-oxobutanoate
• 英文别名: ethyl 4-[benzyl-[2-[(4-carbamimidoylphenyl)methyl]-4-methyl-3-oxo-1,4-benzoxazin-7-yl]amino]-4-oxobutanoate
• CAS: 1026018-10-9
• 化学式: C₃₀H₃₂N₄O₅
• 分子量: 528.608
• InChiKey: RHTVFGOGZVVLBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-4-oxobutanoate 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以82.3%的产率得到4-(Benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  Novel Potent and Selective Thrombin Inhibitors Based on a Central 1,4-Benzoxazin-3(4H)-one Scaffold

  摘要：

  Novel thrombin inhibitors with the central 1,4-benzoxazine-3(4H)-one scaffold, benzamidine P-1 arginine side chain mimetic and various P-3 moieties are described. 3-(Benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-3-oxopropanoic acid (7b), the most potent compound in the series, exhibited a K-i of 2.6 nM in vitro for thrombin and high selectivity against trypsin and factor Xa.

  DOI：

  10.1021/jm701622y
• 作为产物：
  描述：

  ethyl 4-(benzyl(2-(4-cyanobenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-4-oxobutanoate 在 盐酸 、 乙酸铵 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以49.8%的产率得到Ethyl 4-(benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-4-oxobutanoate
  参考文献：
  名称：

  Novel Potent and Selective Thrombin Inhibitors Based on a Central 1,4-Benzoxazin-3(4H)-one Scaffold

  摘要：

  Novel thrombin inhibitors with the central 1,4-benzoxazine-3(4H)-one scaffold, benzamidine P-1 arginine side chain mimetic and various P-3 moieties are described. 3-(Benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-3-oxopropanoic acid (7b), the most potent compound in the series, exhibited a K-i of 2.6 nM in vitro for thrombin and high selectivity against trypsin and factor Xa.

  DOI：

  10.1021/jm701622y

文献信息

• Novel Potent and Selective Thrombin Inhibitors Based on a Central 1,4-Benzoxazin-3(4<i>H</i>)-one Scaffold
  作者：Janez Ilaš、Tihomir Tomašić、Danijel Kikelj

  DOI：10.1021/jm701622y

  日期：2008.5.1

  Novel thrombin inhibitors with the central 1,4-benzoxazine-3(4H)-one scaffold, benzamidine P-1 arginine side chain mimetic and various P-3 moieties are described. 3-(Benzyl(2-(4-carbamimidoylbenzyl)-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)amino)-3-oxopropanoic acid (7b), the most potent compound in the series, exhibited a K-i of 2.6 nM in vitro for thrombin and high selectivity against trypsin and factor Xa.