(3S,6S)-3,6-diiso-butyl-4-((1S,2S)-2-phenylcyclopropanecarbonyl)piperazin-2-one | 1552272-56-6

• 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: (3S,6S)-3,6-diiso-butyl-4-((1S,2S)-2-phenylcyclopropanecarbonyl)piperazin-2-one
• 英文别名: (3S,6S)-3,6-diisobutyl-4-[(1S,2S)-2-phenylcyclopropanecarbonyl]piperazin-2-one；(3S,6S)-3,6-bis(2-methylpropyl)-4-[(1S,2S)-2-phenylcyclopropanecarbonyl]piperazin-2-one
• CAS: 1552272-56-6
• 化学式: C₂₂H₃₂N₂O₂
• 分子量: 356.508
• InChiKey: QWAYUNUQNGRNBW-YRPNKDGESA-N

物化性质

• 沸点：
  554.5±50.0 °C(predicted)
• 密度：
  1.058±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 、 (3S,6S)-3,6-diisobutylpiperazin-2-one 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 反应 3.0h， 以25%的产率得到( 3S,6S)-3,6-diiso-butyl-4-((1R,2R)-2-phenylcyclopropanecarbonyl)piperazin-2-one
  参考文献：
  名称：

  Discovery of a Novel Class of Potent HCV NS4B Inhibitors: SAR Studies on Piperazinone Derivatives

  摘要：

  HTS screening identified compound 2a (piper-azinone derivative) as a low micromolar HCV genotype 1 (GT-1) inhibitor. Resistance mapping studies suggested that this piperazinone chemotype targets the HCV nonstructural protein NS4B. Extensive SAR studies were performed around 2a and the amide function and the C-3/C-6 cis stereochemistry of the piperazinone core were essential for HCV activity. A 10-fold increase in GT-1 potency was observed when the chiral phenylcyclopropyl amide side chain of 2a was replaced with p-fluorophenylisoxazole-carbonyl moiety (67). Replacing the C-6 nonpolar hydrophobic moiety of 67 with a phenyl moiety (95) did not diminish the GT-1 potency. A heterocyclic thiophene moiety (103) and an isoxazole moiety (108) were incorporated as isosteric replacements for the C-6 phenyl moiety (95), resulting in significant improvement in GT-1b and la potency. However, the piperazonone class of compounds lacks GT-2 activity and, consequently, were not pursued further into development.

  DOI：

  10.1021/jm4012643