N-[(E)-(2R,3R,6S)-3-Benzyl-2-hydroxy-6-methanesulfonylamino-7-(naphthalene-2-sulfinyl)-hept-4-enyl]-N-isobutyl-4-nitro-benzenesulfonamide | 1026361-93-2

• 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: N-[(E)-(2R,3R,6S)-3-Benzyl-2-hydroxy-6-methanesulfonylamino-7-(naphthalene-2-sulfinyl)-hept-4-enyl]-N-isobutyl-4-nitro-benzenesulfonamide
• 英文别名: N-[(E,2R,3R,6S)-3-benzyl-2-hydroxy-6-(methanesulfonamido)-7-naphthalen-2-ylsulfinylhept-4-enyl]-N-(2-methylpropyl)-4-nitrobenzenesulfonamide
• CAS: 1026361-93-2
• 化学式: C₃₅H₄₁N₃O₈S₃
• 分子量: 727.924
• InChiKey: STQPOHWODMJLJX-SYNFFWRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  203
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-[(E)-(2R,3R,6S)-3-Benzyl-2-hydroxy-6-methanesulfonylamino-7-(naphthalene-2-sulfinyl)-hept-4-enyl]-N-isobutyl-4-nitro-benzenesulfonamide 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 以2.71 mg的产率得到TYB2
  参考文献：
  名称：

  Reduction of Peptide Character of HIV Protease Inhibitors That Exhibit Nanomolar Potency against Multidrug Resistant HIV-1 Strains

  摘要：

  Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only potent enzyme inhibitors (K-i = 0.12 nM and 0.10 nM, respectively) but also strong anti-HIV agents (IC50 = 9.5 nM and 66 nM, respectively), even against viral strains with multidrug resistance. Furthermore, insertion of an (E)-alkene dipeptide isostere at the P-1-P-2 position of TYB5 led to development of a purely nonpeptidic protease inhibitor, TYB1 (K-i = 0.38 nM, IC50 = 160 nM).

  DOI：

  10.1021/jm020537i
• 作为产物：
  描述：

  N-[1(S)-(2-naphthylthiomethyl)-4(R)-[2(R,S)-oxiranyl]-5-phenylpent-2(E)-enyl](phenylmethoxy)formamide 在 三氟乙酸 sodium periodate 、 茴香硫醚 、 1,2-乙二硫醇 、 间甲酚 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 66.0h， 生成 N-[(E)-(2R,3R,6S)-3-Benzyl-2-hydroxy-6-methanesulfonylamino-7-(naphthalene-2-sulfinyl)-hept-4-enyl]-N-isobutyl-4-nitro-benzenesulfonamide
  参考文献：
  名称：

  Reduction of Peptide Character of HIV Protease Inhibitors That Exhibit Nanomolar Potency against Multidrug Resistant HIV-1 Strains

  摘要：

  Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only potent enzyme inhibitors (K-i = 0.12 nM and 0.10 nM, respectively) but also strong anti-HIV agents (IC50 = 9.5 nM and 66 nM, respectively), even against viral strains with multidrug resistance. Furthermore, insertion of an (E)-alkene dipeptide isostere at the P-1-P-2 position of TYB5 led to development of a purely nonpeptidic protease inhibitor, TYB1 (K-i = 0.38 nM, IC50 = 160 nM).

  DOI：

  10.1021/jm020537i