4-({28-[1,1-dimethylethyl-(2-aminoethyl)carbamate]-28-oxolup-20,29-en-3β-yl}oxy)-2,2-dimethyl-4-oxobutanoic acid | 1426661-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-({28-[1,1-dimethylethyl-(2-aminoethyl)carbamate]-28-oxolup-20,29-en-3β-yl}oxy)-2,2-dimethyl-4-oxobutanoic acid
• 英文别名: N-[O3-(3-carboxy-3-methylbutyryl)betulinyl]-N'-Boc-ethylenediamine；4-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylcarbamoyl]-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid
• CAS: 1426661-79-1
• 化学式: C₄₃H₇₀N₂O₇
• 分子量: 727.038
• InChiKey: MTDPDXYNXDSASU-SYQCDDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-({28-[1,1-dimethylethyl-(2-aminoethyl)carbamate]-28-oxolup-20,29-en-3β-yl}oxy)-2,2-dimethyl-4-oxobutanoic acid 在 2,6-二甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 1.5h， 以45 mg的产率得到4-({28-[(2-aminoethyl)amino]-28-oxolup-20,29-en-3β-yl}oxy)-2,2-dimethyl-4-oxobutanoic acid
  参考文献：
  名称：

  Derivatives of 3-O-(3',3'-dimethylsuccinyl)-betulinic acid

  摘要：

  公开号：

  EP2567965B1
• 作为产物：
  描述：

  白桦脂酸 在 4-二甲氨基吡啶 、 (benzotriazol-1-yloxy)tripyrrolodinophosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 102.0h， 生成 4-({28-[1,1-dimethylethyl-(2-aminoethyl)carbamate]-28-oxolup-20,29-en-3β-yl}oxy)-2,2-dimethyl-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of a new derivative of bevirimat that targets the Gag CA-SP1 cleavage site

  摘要：

  Bevirimat (2), the first-in-class HIV-1 maturation inhibitor, shows a low efficacy due essentially to the natural polymorphism of its target, the CA-SP1 junction. Moreover, its low hydrosolubility makes it difficult to study its interaction with the CA-SP1 junction. We have synthesized new derivatives of bevirimat by adding different hydrophilic substituents at the C-28 position to improve their hydrosolubility and perform the structural study of a complex by NMR. Synthesis of the new derivatives, the effect of substituents at the C-28 position and their hydrosolubility are discussed. The ability of these molecules to inhibit viral infection and their cytotoxicity is assessed. Compared to the well-known bevirimat (2), one of our compounds (16) shows a higher hydrosolubility associated with a 2.5 fold increase in activity, a higher selectivity index and a better antiviral profile. Moreover, for the first time a direct interaction between a derivative of bevirimat (16) and the domain CA-SP1 NC is shown by NMR. Information from this study should allow us to decipher the mechanism by which bevirimat inhibits HIV-1 maturation and how the natural polymorphism of the spacer peptide SP1 triggers resistance to inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.013