(2S)-6-(dibenzylcarbamoylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-6-(dibenzylcarbamoylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid
• 英文别名: (2S)-6-(dibenzylcarbamoylamino)-2-[(4-methylphenyl)sulfonyl-(2-methylpropyl)amino]hexanoic acid
• 化学式: C₃₂H₄₁N₃O₅S
• 分子量: 579.761
• InChiKey: VSCUBCGPKBGSHX-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine 在 sodium hydroxide 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-6-(dibenzylcarbamoylamino)-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid
  参考文献：
  名称：

  Lysine sulfonamides as novel HIV-Protease inhibitors: optimization of the Nε -acyl-phenyl spacer

  摘要：

  A series of Nalpha-isobutyl-Nalpha-arylsulfonamido-(Nepsilon acyl) lysine and lysinol derivatives were prepared and evaluated as inhibitors of HIV protease and wild type virus. A simple original synthesis was devised to form Nalpha-(arylsulfonamide)-Nalpha-isobutyI lysine, which could be easily acylated with carboxylic acids at the NE position. A two-atom spacer was found to be optimal between this acyl group and a phenyl yielding compounds of sub-nanomolar potency on purified enzyme. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.058

文献信息

• Lysine sulfonamides as novel HIV-protease inhibitors: Nε-disubstituted ureas
  作者：Brent R Stranix、Gilles Sauvé、Abderrahim Bouzide、Alexandre Coté、Guy Sévigny、Jocelyn Yelle、Valérie Perron

  DOI：10.1016/j.bmcl.2004.05.049

  日期：2004.8

  A series of lysine sulfonamide analogues bearing a Nepsilon-benzylic ureas was synthesized using both solution-phase and solid-phase approaches. A novel synthetic route of Nalpha-(alkyl)-Nalpha-(sulfonamides)lysinol using alpha-amino-caprolactam was developed. Evaluation of these novel protease inhibitors revealed compounds with high potency against wild-type HIV virus. (C) 2004 Elsevier Ltd. All rights reserved.
• Lysine sulfonamides as novel HIV-Protease inhibitors: optimization of the Nε -acyl-phenyl spacer
  作者：Brent R. Stranix、Gilles Sauvé、Abderrahim Bouzide、Alexandre Coté、Guy Sévigny、Jocelyn Yelle

  DOI：10.1016/j.bmcl.2003.09.058

  日期：2003.12

  A series of Nalpha-isobutyl-Nalpha-arylsulfonamido-(Nepsilon acyl) lysine and lysinol derivatives were prepared and evaluated as inhibitors of HIV protease and wild type virus. A simple original synthesis was devised to form Nalpha-(arylsulfonamide)-Nalpha-isobutyI lysine, which could be easily acylated with carboxylic acids at the NE position. A two-atom spacer was found to be optimal between this acyl group and a phenyl yielding compounds of sub-nanomolar potency on purified enzyme. (C) 2003 Elsevier Ltd. All rights reserved.