N'-hydroxy-N-pyren-2-yloctanediamide | 1219807-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N'-hydroxy-N-pyren-2-yloctanediamide
• CAS: 1219807-96-1
• 化学式: C₂₄H₂₄N₂O₃
• 分子量: 388.466
• InChiKey: XDJULMRABPHMMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Methyl 8-oxo-8-(pyren-2-ylamino)octanoate 在 羟胺 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 N'-hydroxy-N-pyren-2-yloctanediamide
  参考文献：
  名称：

  Modified Cap Group Suberoylanilide Hydroxamic Acid Histone Deacetylase Inhibitor Derivatives Reveal Improved Selective Antileukemic Activity

  摘要：

  A series of SAHA cap derivatives was designed and prepared in good-to-excellent yields that varied from 49% to 95%. These derivatives were evaluated for their antiproliferative activity in several human cancer cell lines. Antiproliferative activity was observed for concentrations varying from 0.12 to > 100 mu M, and a molecular modeling approach of selected SAHA derivatives, based on available structural information of human HDAC8 in complex with SAHA, was performed. Strikingly, two compounds displayed up to 10-fold improved antileukemic activity with respect to SAHA; however, these compounds displayed antiproliferative activity similar to SAHA when assayed against solid tumor-derived cell lines. A 10-fold improvement in the leukemic vs peripheral blood mononuclear cell therapeutic ratio, with no evident in vivo toxicity toward blood cells, was also observed. The herein-described compounds and method of synthesis will provide invaluable tools to investigate the molecular mechanism responsible for the reported selectively improved antileukemic activity.

  DOI：

  10.1021/jm901358y