2-((2-((4-carbamimidoylphenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl)(3,5-difluorobenzyl)amino)acetic acid | 1370705-97-7

• 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: 2-((2-((4-carbamimidoylphenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl)(3,5-difluorobenzyl)amino)acetic acid
• 英文别名: 2-[[2-[(4-carbamimidoylphenoxy)methyl]-2,4-dimethyl-3H-1,4-benzoxazin-6-yl]-[(3,5-difluorophenyl)methyl]amino]acetic acid
• CAS: 1370705-97-7
• 化学式: C₂₇H₂₈F₂N₄O₄
• 分子量: 510.541
• InChiKey: JJCBUVHDWHZUID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-[(6-amino-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methoxy]benzonitrile 在 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.5h， 生成 2-((2-((4-carbamimidoylphenoxy)methyl)-2,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-6-yl)(3,5-difluorobenzyl)amino)acetic acid
  参考文献：
  名称：

  Fluorinated dual antithrombotic compounds based on 1,4-benzoxazine scaffold

  摘要：

  Fluorinated 3,4-dihydro-2H-1,4-benzoxazine derivatives possessing both thrombin inhibitory and glycoprotein IIb/IIIa receptor antagonistic activities were prepared as potential dual antithrombotic compounds. Fluorine scan (3-fluorobenzyl, 4-fluorobenzyl, 3,4-difluorobenzyl and 3,5-difluorobenzyl substituted compounds) was performed in order to obtain 6-(carboxymethyl)(3,4-difluorobenzyl) amino compound (9i) as the most potent compound with balanced dual activity (K-i(Thr) = 0.33 +/- 0.07 mu M, IC50(GP IIb/IIIa) = 1.1 +/- 0.6 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.059

文献信息

• Fluorinated dual antithrombotic compounds based on 1,4-benzoxazine scaffold
  作者：Miloš Ilić、Danijel Kikelj、Janez Ilaš

  DOI：10.1016/j.ejmech.2012.01.059

  日期：2012.4

  Fluorinated 3,4-dihydro-2H-1,4-benzoxazine derivatives possessing both thrombin inhibitory and glycoprotein IIb/IIIa receptor antagonistic activities were prepared as potential dual antithrombotic compounds. Fluorine scan (3-fluorobenzyl, 4-fluorobenzyl, 3,4-difluorobenzyl and 3,5-difluorobenzyl substituted compounds) was performed in order to obtain 6-(carboxymethyl)(3,4-difluorobenzyl) amino compound (9i) as the most potent compound with balanced dual activity (K-i(Thr) = 0.33 +/- 0.07 mu M, IC50(GP IIb/IIIa) = 1.1 +/- 0.6 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.