2-[3-[(2S,5S)-7-[2-(1H-indol-3-yl)ethyl]-10-(3-methylbut-2-enyl)-3,6,9,13-tetraoxo-5-(6-oxooctyl)-1,4,7,10-tetrazacyclotridec-2-yl]propyl]guanidine | 1393817-17-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 2-[3-[(2S,5S)-7-[2-(1H-indol-3-yl)ethyl]-10-(3-methylbut-2-enyl)-3,6,9,13-tetraoxo-5-(6-oxooctyl)-1,4,7,10-tetrazacyclotridec-2-yl]propyl]guanidine
• CAS: 1393817-17-8
• 化学式: C₃₆H₅₄N₈O₅
• 分子量: 678.875
• InChiKey: XIJUBGRWSWKSLJ-CONSDPRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  196
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 哌啶 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 2-[3-[(2S,5S)-7-[2-(1H-indol-3-yl)ethyl]-10-(3-methylbut-2-enyl)-3,6,9,13-tetraoxo-5-(6-oxooctyl)-1,4,7,10-tetrazacyclotridec-2-yl]propyl]guanidine
  参考文献：
  名称：

  Macrocyclic Peptoid–Peptide Hybrids as Inhibitors of Class I Histone Deacetylases

  摘要：

  We report the design, synthesis, and biological evaluation of the first macrocyclic peptoid-containing histone deacetylase (HDAC) inhibitors. The compounds selectively inhibit human class I HDAC isoforms in vitro, with no inhibition of the tubulin deacetylase activity associated with class IIb HDAC6 in cultured Jurkat cells. Compared to the natural product apicidin (1), one inhibitor (compound 10) showed equivalent potency against K-562 cells, but was more cytoselective across a panel of cancer cell lines.

  DOI：

  10.1021/ml300162r

文献信息

• Macrocyclic Peptoid–Peptide Hybrids as Inhibitors of Class I Histone Deacetylases
  作者：Christian A. Olsen、Ana Montero、Luke J. Leman、M. Reza Ghadiri

  DOI：10.1021/ml300162r

  日期：2012.9.13

  We report the design, synthesis, and biological evaluation of the first macrocyclic peptoid-containing histone deacetylase (HDAC) inhibitors. The compounds selectively inhibit human class I HDAC isoforms in vitro, with no inhibition of the tubulin deacetylase activity associated with class IIb HDAC6 in cultured Jurkat cells. Compared to the natural product apicidin (1), one inhibitor (compound 10) showed equivalent potency against K-562 cells, but was more cytoselective across a panel of cancer cell lines.