{(S)-1-[(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-1-hydroxymethyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester | 253344-35-3

• 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: {(S)-1-[(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-1-hydroxymethyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S)-1-benzyl-2-[[(3S)-3-[[(2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoyl]amino]-4-hydroxy-butyl]amino]-2-oxo-ethyl]carbamate；tert-butyl N-[(2S)-1-[[(2S)-1-hydroxy-4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]butan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 253344-35-3
• 化学式: C₃₂H₄₆N₄O₇
• 分子量: 598.74
• InChiKey: ODJKKCSQQNRDSH-GSDHBNRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-1-hydroxymethyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 苯甲醚 为溶剂， 以89%的产率得到(S)-2-Amino-N-[(S)-3-((S)-2-amino-3-phenyl-propionylamino)-1-hydroxymethyl-propyl]-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：

  BOC-L-苯丙氨酸琥珀酰亚胺酯 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成 {(S)-1-[(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-1-hydroxymethyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
  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.