(S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl-(toluene-4-sulfonyl)-amino]-butyric acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl-(toluene-4-sulfonyl)-amino]-butyric acid
• 英文别名: (2S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl(p-tolylsulfonyl)amino]butanoic acid；(2S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(4-methylphenyl)sulfonyl-(2-methylpropyl)amino]butanoic acid
• 化学式: C₃₀H₃₄N₂O₆S
• 分子量: 550.676
• InChiKey: ZBPGHMQQCBXZHV-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-2-[Isobutyl-(toluene-4-sulfonyl)-amino]-4-(toluene-4-sulfonyloxy)-butyric acid methyl ester 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-[isobutyl-(toluene-4-sulfonyl)-amino]-butyric acid
  参考文献：
  名称：

  Lysine derivatives as potent HIV protease inhibitors. Discovery, synthesis and structure–activity relationship studies

  摘要：

  A screening assay program on HIV-protease was carried out on more than fifty commercially available N-protected amino acids and has revealed that those with a long side chain such as lysine, ornithine and arginine exhibited significant inhibition of HIV protease enzyme. The presence of an Fmoc group was found to be essential to obtain micromolar inhibitors and the addition of an alkyl group at the N alpha-position resulted in the discovery of the lead compound 11 displaying a 5 nM inhibition constant. Although this new inhibitor series is not categorized among those mimicking the substrate with a non-hydrolyzable transition-state isoster, it was found very specific to inhibit HIV protease enzyme in comparison to the mammalian aspartyl proteases pepsin, renin and cathepsin. Furthermore, these inhibitors did not show any cytotoxicity at a concentration below 75 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.068