ditert-butyl (2S)-2-[[(2S)-3-amino-1,1,1-trifluoropropan-2-yl]amino]butanedioate | 1422544-50-0

• 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: ditert-butyl (2S)-2-[[(2S)-3-amino-1,1,1-trifluoropropan-2-yl]amino]butanedioate
• CAS: 1422544-50-0
• 化学式: C₁₅H₂₇F₃N₂O₄
• 分子量: 356.386
• InChiKey: VQKWSVIODDQXNR-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2S)-2-[[(2S)-3-amino-1,1,1-trifluoropropan-2-yl]amino]butanedioate 在 哌啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.3h， 生成
  参考文献：
  名称：

  Linear Trifluoroethylamine RGD Peptidomimetics: Stereoselective Synthesis and Integrin αvβ3 Affinity

  摘要：

  The Arg-Gly-Asp (RGD) tripeptide is the smallest recognition sequence for the alpha(v)beta(3) integrin receptor. A number of non-peptide analogues of the RGD linear sequence, some of them having improved pharmacological properties, have been proposed in the last two decades. In this study, the stereogenic trifluoroethylamine function was employed as peptide bond surrogate for the development of a new class of RGD peptide mimics. In fact, the trifluoroethylamine group was shown to behave as a peptide-bond surrogate maintaining the H-bond donor capacity of the NH peptide group and a CH(CF3)NH backbone angle close to the native peptide bond 120 degrees. The trifluoroethylamine function is also known to display high metabolic stability and in some cases it positively affects ligand-receptor interactions. Two linear Psi[CH(CF3)NH]Gly-RGD diastereoisomers were synthesized with good stereocontrol and submitted to biological assays. A remarkable loss in alpha(v)beta(3) integrin affinity was observed for both compounds, suggesting that the bulky CF3 moiety is not well tolerated within the alpha(v)beta(3) binding pocket.

  DOI：

  10.1055/s-0032-1317557
• 作为产物：
  描述：

  ditert-butyl (2S)-2-[[(2S)-1,1,1-trifluoro-3-nitropropan-2-yl]amino]butanedioate 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到ditert-butyl (2S)-2-[[(2S)-3-amino-1,1,1-trifluoropropan-2-yl]amino]butanedioate
  参考文献：
  名称：

  Linear Trifluoroethylamine RGD Peptidomimetics: Stereoselective Synthesis and Integrin αvβ3 Affinity

  摘要：

  The Arg-Gly-Asp (RGD) tripeptide is the smallest recognition sequence for the alpha(v)beta(3) integrin receptor. A number of non-peptide analogues of the RGD linear sequence, some of them having improved pharmacological properties, have been proposed in the last two decades. In this study, the stereogenic trifluoroethylamine function was employed as peptide bond surrogate for the development of a new class of RGD peptide mimics. In fact, the trifluoroethylamine group was shown to behave as a peptide-bond surrogate maintaining the H-bond donor capacity of the NH peptide group and a CH(CF3)NH backbone angle close to the native peptide bond 120 degrees. The trifluoroethylamine function is also known to display high metabolic stability and in some cases it positively affects ligand-receptor interactions. Two linear Psi[CH(CF3)NH]Gly-RGD diastereoisomers were synthesized with good stereocontrol and submitted to biological assays. A remarkable loss in alpha(v)beta(3) integrin affinity was observed for both compounds, suggesting that the bulky CF3 moiety is not well tolerated within the alpha(v)beta(3) binding pocket.

  DOI：

  10.1055/s-0032-1317557