tert-butyl 2(S)-amino-3-[5-(4-(N-(tert-butyloxycarbonyl)pyridin-2-ylamino)butyl)isoxazolin-3-ylcarbonyl]aminopropionate | 185563-90-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 2(S)-amino-3-[5-(4-(N-(tert-butyloxycarbonyl)pyridin-2-ylamino)butyl)isoxazolin-3-ylcarbonyl]aminopropionate
• 英文别名: tert-butyl (2S)-2-amino-3-[[5-[4-[(2-methylpropan-2-yl)oxycarbonyl-pyridin-2-ylamino]butyl]-4,5-dihydro-1,2-oxazole-3-carbonyl]amino]propanoate
• CAS: 185563-90-0
• 化学式: C₂₅H₃₉N₅O₆
• 分子量: 505.615
• InChiKey: OBTGKVVVCSOGOS-ZVAWYAOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 2(S)-amino-3-[5-(4-(N-(tert-butyloxycarbonyl)pyridin-2-ylamino)butyl)isoxazolin-3-ylcarbonyl]aminopropionate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 2-[(S)-4-isopropylbenzenesulfonylamino]-3-[5-(4-((pyridin-2-yl)amino)butyl)isoxazolin-3-ylcarbonyl]aminopropionic acid trifluoroacetate
  参考文献：
  名称：

  Isoxazolines as Potent Antagonists of the Integrin α_vβ₃

  摘要：

  Starting with lead compound 2, we sought to increase the selectivity for alpha(v)beta(3)-mediated cell adhesion by examining the effects of structural changes in both the guanidine mimetic and the substituent alpha to the carboxylate. To prepare some of the desired aminoimidazoles, a novel reductive amination utilizing a trityl-protected aminoimidazole was developed. It was found that guanidine mimetics with a wide range of pK(a)'s were potent antagonists of alpha(v)beta(3). In general, it appeared that an acylated 2-aminoimidazole guanidine mimetic imparted excellent selectivity for alpha(v)beta(3)-mediated adhesion versus alpha(IIb)beta(3)-mediated platelet aggregation, with selectivity of approximately 3 orders of magnitude observed for compounds 3g and 3h. It was also found in this series that the alpha-substituent was required for potent activity and that 2,6-disubstituted arylsulfonamides were optimal. In addition, the selective alpha(v)beta(3) antagonist 3h was found to be a potent inhibitor of alpha(v)beta(3)-mediated cell migration.

  DOI：

  10.1021/jm9900321
• 作为产物：
  描述：

  5-己烯-1-醇 在 Pd-BaSO₄ N-甲基吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 氢气 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、282.69 kPa 条件下， 反应 67.75h， 生成 tert-butyl 2(S)-amino-3-[5-(4-(N-(tert-butyloxycarbonyl)pyridin-2-ylamino)butyl)isoxazolin-3-ylcarbonyl]aminopropionate
  参考文献：
  名称：

  Isoxazolines as Potent Antagonists of the Integrin α_vβ₃

  摘要：

  Starting with lead compound 2, we sought to increase the selectivity for alpha(v)beta(3)-mediated cell adhesion by examining the effects of structural changes in both the guanidine mimetic and the substituent alpha to the carboxylate. To prepare some of the desired aminoimidazoles, a novel reductive amination utilizing a trityl-protected aminoimidazole was developed. It was found that guanidine mimetics with a wide range of pK(a)'s were potent antagonists of alpha(v)beta(3). In general, it appeared that an acylated 2-aminoimidazole guanidine mimetic imparted excellent selectivity for alpha(v)beta(3)-mediated adhesion versus alpha(IIb)beta(3)-mediated platelet aggregation, with selectivity of approximately 3 orders of magnitude observed for compounds 3g and 3h. It was also found in this series that the alpha-substituent was required for potent activity and that 2,6-disubstituted arylsulfonamides were optimal. In addition, the selective alpha(v)beta(3) antagonist 3h was found to be a potent inhibitor of alpha(v)beta(3)-mediated cell migration.

  DOI：

  10.1021/jm9900321