(2R,4S)-2-benzyl-5-[(2S)-2,8-dibenzyl-4-oxo-3,8-diazaspiro[4.5]decan-3-yl]-4-hydroxy-N-[(1S,2R)-2-hydroxyindan-1-yl]pentanamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2R,4S)-2-benzyl-5-[(2S)-2,8-dibenzyl-4-oxo-3,8-diazaspiro[4.5]decan-3-yl]-4-hydroxy-N-[(1S,2R)-2-hydroxyindan-1-yl]pentanamide
• 英文别名: (2R,4S)-2-benzyl-5-[(3S)-3,8-dibenzyl-1-oxo-2,8-diazaspiro[4.5]decan-2-yl]-4-hydroxy-N-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]pentanamide
• 化学式: C₄₃H₄₉N₃O₄
• 分子量: 671.88
• InChiKey: JQIJNYFNVGXAFQ-WQHHGGELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl (4R)-4-[(tert-butoxycarbonyl) amino]-5-phenylpentanoate 在 盐酸 、 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.75h， 生成 (2R,4S)-2-benzyl-5-[(2S)-2,8-dibenzyl-4-oxo-3,8-diazaspiro[4.5]decan-3-yl]-4-hydroxy-N-[(1S,2R)-2-hydroxyindan-1-yl]pentanamide
  参考文献：
  名称：

  Novel spirocyclic pyrrolidones as P2/P1 mimetics in potent inhibitors of HIV-1 protease

  摘要：

  We have developed concise and efficient syntheses of novel spirocyclic pyrrolidones 1-3, which involve the alkylation of pyrrolidone precursor 13 with 1.5-dibromopentane, 16 and 15, followed by an in situ lactamization. Conjugates of 1 and 2 with P1'/P2' hydroxy-indanolamine moiety resulted in novel and potent inhibitors of HTV-1 protease 25 and 26. suggesting that 1 and 2 are novel P2/P1 HIV-P1 mimetics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00733-3

文献信息

• Novel spirocyclic pyrrolidones as P2/P1 mimetics in potent inhibitors of HIV-1 protease
  作者：Wieslaw M. Kazmierski、Eric Furfine、Andrew Spaltenstein、Lois L. Wright

  DOI：10.1016/s0960-894x(02)00733-3

  日期：2002.12

  We have developed concise and efficient syntheses of novel spirocyclic pyrrolidones 1-3, which involve the alkylation of pyrrolidone precursor 13 with 1.5-dibromopentane, 16 and 15, followed by an in situ lactamization. Conjugates of 1 and 2 with P1'/P2' hydroxy-indanolamine moiety resulted in novel and potent inhibitors of HTV-1 protease 25 and 26. suggesting that 1 and 2 are novel P2/P1 HIV-P1 mimetics. (C) 2002 Elsevier Science Ltd. All rights reserved.