N-[(3R,4R,7S,20S,27R,28R,31S,44S)-4,15,28,39-tetramethyl-2,6,13,16,19,26,30,37,40,43-decaoxo-27-(quinoline-3-carbonylamino)-1,5,12,15,18,25,29,36,39,42-decazapentacyclo[42.4.0.07,12.020,25.031,36]octatetracontan-3-yl]quinoline-3-carboxamide | 1499188-39-4

• 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: N-[(3R,4R,7S,20S,27R,28R,31S,44S)-4,15,28,39-tetramethyl-2,6,13,16,19,26,30,37,40,43-decaoxo-27-(quinoline-3-carbonylamino)-1,5,12,15,18,25,29,36,39,42-decazapentacyclo[42.4.0.07,12.020,25.031,36]octatetracontan-3-yl]quinoline-3-carboxamide
• CAS: 1499188-39-4
• 化学式: C₆₂H₇₈N₁₄O₁₂
• 分子量: 1211.39
• InChiKey: PZGLVWQIOPPCMW-SUDTZTPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  88
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  322
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  benzyl N-[(3R,4R,7S,20S,27R,28R,31S,44S)-4,15,28,39-tetramethyl-2,6,13,16,19,26,30,37,40,43-decaoxo-27-(phenylmethoxycarbonylamino)-1,5,12,15,18,25,29,36,39,42-decazapentacyclo[42.4.0.07,12.020,25.031,36]octatetracontan-3-yl]carbamate 在 10% palladium hydroxide on charcoal 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-[(3R,4R,7S,20S,27R,28R,31S,44S)-4,15,28,39-tetramethyl-2,6,13,16,19,26,30,37,40,43-decaoxo-27-(quinoline-3-carbonylamino)-1,5,12,15,18,25,29,36,39,42-decazapentacyclo[42.4.0.07,12.020,25.031,36]octatetracontan-3-yl]quinoline-3-carboxamide
  参考文献：
  名称：

  Total Synthesis of Quinaldopeptin and Its Analogues

  摘要：

  The first total synthesis of quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.

  DOI：

  10.1021/jo402267r

文献信息

• Total Synthesis of Quinaldopeptin and Its Analogues
  作者：Satoshi Ichikawa、Takuya Okamura、Akira Matsuda

  DOI：10.1021/jo402267r

  日期：2013.12.20

  The first total synthesis of quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.