(6S)-4-(1-benzofuran-2-ylmethyl)-6-benzyl-1-[(4-methylphenyl)methyl]piperazin-2-one | 1186504-66-4

• 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: (6S)-4-(1-benzofuran-2-ylmethyl)-6-benzyl-1-[(4-methylphenyl)methyl]piperazin-2-one
• CAS: 1186504-66-4
• 化学式: C₂₈H₂₈N₂O₂
• 分子量: 424.543
• InChiKey: QFUNALOZTHXHBW-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (6S)-6-benzyl-1-[(4-methylphenyl)methyl]piperazin-2-one 、 苯并[b]呋喃-2-甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (6S)-4-(1-benzofuran-2-ylmethyl)-6-benzyl-1-[(4-methylphenyl)methyl]piperazin-2-one
  参考文献：
  名称：

  Characterization of lassa virus cell entry inhibitors: Determination of the active enantiomer by asymmetric synthesis

  摘要：

  The comparative characterization of a series of 4-acyl-1,6-dialkylpiperazin-2-ones as potent cell entry inhibitors of the hemorrhagic fever arenavirus Lassa (LASV) is disclosed. The resolution and examination of the individual enantiomers of the prototypical LASV cell entry inhibitor 3 (16G8) is reported and the more potent (-)-enantiomer was found to be 15-fold more active than the corresponding (+)-enantiomer. The absolute configuration of (-)-3 was established by asymmetric synthesis of the active inhibitor (-)-(S)-3 (lassamycin-1). A limited deletion scan of lassamycin-1 defined key structural features required of the prototypical inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.098

文献信息

• Characterization of lassa virus cell entry inhibitors: Determination of the active enantiomer by asymmetric synthesis
  作者：Landon R. Whitby、Andrew M. Lee、Stefan Kunz、Michael B.A. Oldstone、Dale L. Boger

  DOI：10.1016/j.bmcl.2009.04.098

  日期：2009.7

  The comparative characterization of a series of 4-acyl-1,6-dialkylpiperazin-2-ones as potent cell entry inhibitors of the hemorrhagic fever arenavirus Lassa (LASV) is disclosed. The resolution and examination of the individual enantiomers of the prototypical LASV cell entry inhibitor 3 (16G8) is reported and the more potent (-)-enantiomer was found to be 15-fold more active than the corresponding (+)-enantiomer. The absolute configuration of (-)-3 was established by asymmetric synthesis of the active inhibitor (-)-(S)-3 (lassamycin-1). A limited deletion scan of lassamycin-1 defined key structural features required of the prototypical inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.