3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((2-((methylsulfonyl)amino)-3-(2-naphthalenylthio)-1-oxopropyl)amino)-4-phenylbutyl)-, (3S-(2(2S*,3R*(R*)),3alpha,4abeta,8abeta))- | 159878-29-2

• 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: 3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((2-((methylsulfonyl)amino)-3-(2-naphthalenylthio)-1-oxopropyl)amino)-4-phenylbutyl)-, (3S-(2(2S*,3R*(R*)),3alpha,4abeta,8abeta))-
• 英文别名: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-[[(2S)-2-(methanesulfonamido)-3-naphthalen-2-ylsulfanylpropanoyl]amino]-4-phenylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide
• CAS: 159878-29-2
• 化学式: C₃₈H₅₂N₄O₅S₂
• 分子量: 708.987
• InChiKey: NNBAMFOWJQFHIQ-HHIXDIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((2-((methylsulfonyl)amino)-3-(2-naphthalenylthio)-1-oxopropyl)amino)-4-phenylbutyl)-, (3S-(2(2S*,3R*(R*)),3alpha,4abeta,8abeta))- 在 sodium periodate 作用下， 以 甲醇 为溶剂， 生成 (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-[(2S)-2-methanesulfonamido-3-(naphthalene-2-sulfinyl)propanamido]-4-phenylbutyl]-decahydroisoquinoline-3-carboxamide
  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-叔丁基-十氢异喹啉-3(S)-甲酰胺 在 三甲基溴硅烷 、 三氟乙酸 盐酸 、 茴香硫醚 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 1,2-乙二硫醇 、 间甲酚 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 7.17h， 生成 3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((2-((methylsulfonyl)amino)-3-(2-naphthalenylthio)-1-oxopropyl)amino)-4-phenylbutyl)-, (3S-(2(2S*,3R*(R*)),3alpha,4abeta,8abeta))-
  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