desmethylquinaldopeptin | 1499188-45-2

• 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: desmethylquinaldopeptin
• 英文别名: 3-hydroxy-N-[(3R,7S,20S,27R,31S,44S)-27-[(3-hydroxyquinoline-2-carbonyl)amino]-15,39-dimethyl-2,6,13,16,19,26,30,37,40,43-decaoxo-1,5,12,15,18,25,29,36,39,42-decazapentacyclo[42.4.0.07,12.020,25.031,36]octatetracontan-3-yl]quinoline-2-carboxamide
• CAS: 1499188-45-2
• 化学式: C₆₀H₇₄N₁₄O₁₄
• 分子量: 1215.33
• InChiKey: GWLXUWUJIUZCAN-CNGYLHDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  88
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  363
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  Cbz-D-Dap(1)-Pip-Gly-Sar-Pip-(2).Cbz-D-Dap(2)-Pip-Gly-Sar-Pip-(1) 在 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.5h， 生成 desmethylquinaldopeptin
  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.