(S)-2,3-Bis-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-propionic acid | 253344-32-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-2,3-Bis-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-propionic acid
• 英文别名: (2S)-2,3-bis[[(2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoyl]amino]propanoic acid；(2S)-2,3-bis[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]propanoic acid
• CAS: 253344-32-0
• 化学式: C₃₁H₄₂N₄O₈
• 分子量: 598.696
• InChiKey: XOOGVXSKTCJQSQ-HJOGWXRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2,3-Bis-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-propionic acid 在 N-甲基吗啉 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 苯甲醚 为溶剂， 反应 0.75h， 生成 (S)-2-Amino-N-[(S)-2-((S)-2-amino-3-phenyl-propionylamino)-1-hydroxymethyl-ethyl]-3-phenyl-propionamide
  参考文献：
  名称：

  Symmetry-based inhibitors of HIV-1 protease. Design, synthesis and preliminary structure-activity studies of acylated 2,3-diamino-1-hydroxypropanes and 2,4 diamino-1-hydroxybutanes

  摘要：

  Two series of peptidomimetics containing a novel C-2 pseudosymmetrical hydroxyalkyldiamino core structure were prepared from amino acid starting materials and tested for inhibitory activity against the HIV-1 protease (HN-1 Pr) and the virus in cell culture. In the 2,3-diamino-1-hydroxypropane series, compound 6a, containing P1/P1(I) benzyl and P2/P2(I) Fmoc substituents, displayed modest HTV-1 Pr inhibition (IC50 = 430 nM). The corresponding 2,4-diamino-1-hydroxybutane derivative (6b) was the best inhibitor of the series (IC50 = 160 nM). Interestingly, 6a and 6b showed satisfactory inhibition of HIV replication in cell culture (ED50 = 340 and 110 nM, respectively), a result which suggests good cell membrane penetration by this class of compounds. (C) 1999 editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)80034-3
• 作为产物：
  描述：

  L-2,3-二氨基丙酸 、 BOC-L-苯丙氨酸琥珀酰亚胺酯 在 N-甲基吗啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (S)-2,3-Bis-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-propionic acid
  参考文献：
  名称：

  Symmetry-based inhibitors of HIV-1 protease. Design, synthesis and preliminary structure-activity studies of acylated 2,3-diamino-1-hydroxypropanes and 2,4 diamino-1-hydroxybutanes

  摘要：

  Two series of peptidomimetics containing a novel C-2 pseudosymmetrical hydroxyalkyldiamino core structure were prepared from amino acid starting materials and tested for inhibitory activity against the HIV-1 protease (HN-1 Pr) and the virus in cell culture. In the 2,3-diamino-1-hydroxypropane series, compound 6a, containing P1/P1(I) benzyl and P2/P2(I) Fmoc substituents, displayed modest HTV-1 Pr inhibition (IC50 = 430 nM). The corresponding 2,4-diamino-1-hydroxybutane derivative (6b) was the best inhibitor of the series (IC50 = 160 nM). Interestingly, 6a and 6b showed satisfactory inhibition of HIV replication in cell culture (ED50 = 340 and 110 nM, respectively), a result which suggests good cell membrane penetration by this class of compounds. (C) 1999 editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)80034-3

文献信息

• Symmetry-based inhibitors of HIV-1 protease. Design, synthesis and preliminary structure-activity studies of acylated 2,3-diamino-1-hydroxypropanes and 2,4 diamino-1-hydroxybutanes
  作者：Mauro Marastoni、Martina Bazzaro、Fabrizio Bortolotti、Severo Salvadori、Roberto Tomatis

  DOI：10.1016/s0223-5234(00)80034-3

  日期：1999.7

  Two series of peptidomimetics containing a novel C-2 pseudosymmetrical hydroxyalkyldiamino core structure were prepared from amino acid starting materials and tested for inhibitory activity against the HIV-1 protease (HN-1 Pr) and the virus in cell culture. In the 2,3-diamino-1-hydroxypropane series, compound 6a, containing P1/P1(I) benzyl and P2/P2(I) Fmoc substituents, displayed modest HTV-1 Pr inhibition (IC50 = 430 nM). The corresponding 2,4-diamino-1-hydroxybutane derivative (6b) was the best inhibitor of the series (IC50 = 160 nM). Interestingly, 6a and 6b showed satisfactory inhibition of HIV replication in cell culture (ED50 = 340 and 110 nM, respectively), a result which suggests good cell membrane penetration by this class of compounds. (C) 1999 editions scientifiques et medicales Elsevier SAS.