(R)-sirtinol | 870102-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-sirtinol
• 英文别名: 2-[(2-hydroxynaphthalen-1-yl)methylideneamino]-N-[(1R)-1-phenylethyl]benzamide
• CAS: 870102-75-3
• 化学式: C₂₆H₂₂N₂O₂
• 分子量: 394.473
• InChiKey: UXJFDYIHRJGPFS-GOSISDBHSA-N

物化性质

• 沸点：
  659.2±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Iron(III) nitrate nonahydrate 、 (R)-sirtinol 以 四氢呋喃 为溶剂， 反应 0.5h， 以62%的产率得到[Fe^III(sirtinol-H)(NO₃)₂]
  参考文献：
  名称：

  Sirtuin inhibitor sirtinol is an intracellular iron chelator

  摘要：

  作为sirtuin去乙酰化酶的抑制剂，sirtinol结合细胞内铁并扰乱铁依赖酶核苷酸还原酶的活性位点。

  DOI：

  10.1039/c5cc00829h

文献信息

• Metal-binding effects of sirtuin inhibitor sirtinol
  作者：Eman A. Akam、Ritika Gautam、Elisa Tomat

  DOI：10.1080/10610278.2015.1092537

  日期：2016.2.1

  Sirtinol, a Schiff base derived from 2-hydroxy-1-naphthaldehyde, is an inhibitor of sirtuin proteins, a family of deacetylases active in gene regulation and relevant to the study of cancer growth. The formation of copper(II) and zinc(II) complexes of sirtinol is investigated by spectroscopic and structural methods. The molecular structure of this protein inhibitor allows for coordination of first-row transition metals in both tridentate and bidentate fashion. In addition, assays in cultured breast cancer cells reveal that Cu-II(sirtinol-H)(2) and previously reported Fe-III(sirtinol-H)(NO3)(2) present enhanced cytotoxicity when compared to the free ligand, and that the ferric complex causes an increase in intracellular oxidative stress. Transition metal coordination in the biological milieu could therefore contribute additional effects to the biological profile of sirtinol.