2-(4'-Hydroxybenzyl)-6-hydroxy-1-tetralon | 72861-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(4'-Hydroxybenzyl)-6-hydroxy-1-tetralon
• 英文别名: 6-Hydroxy-2-(4-hydroxy-benzyl)-3,4-dihydro-2H-naphthalen-1-one；6-hydroxy-2-[(4-hydroxyphenyl)methyl]-3,4-dihydro-2H-naphthalen-1-one
• CAS: 72861-95-1
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: FEUVSYIDCDSZQO-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C
• 沸点：
  517.3±45.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-羟基-1-四氢萘酮 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 乙醇 、 乙酸乙酯 、 丁酮 为溶剂， 反应 6.0h， 生成 2-(4'-Hydroxybenzyl)-6-hydroxy-1-tetralon
  参考文献：
  名称：

  Novel Tetralone-Derived Retinoic Acid Metabolism Blocking Agents:  Synthesis and in Vitro Evaluation with Liver Microsomal and MCF-7 CYP26A1 Cell Assays

  摘要：

  The potent inhibitory activity of novel 2-benzyltetralone and 2-benzylidenetetralone derivatives vs liver microsomal retinoic acid metabolizing enzymes and a MCF-7 CYP26A1 cell assay is described. In the liver microsomal assay, the 2-biphenylmethyl-6-hydroxytetralone derivatives 16a and 16b were found to be potent inhibitors (IC50 = 0.5 and 0.8 mu M) compared with the broad spectrum P450 inhibitor ketoconazole and the retinoid mimetic R115866 (IC50 = 18.0 and 9.0 mu M, respectively). In the MCF-7 CYP26A1 cell assay, the 2-(4-hydroxybenzyl)-6-methoxytetralone 5 and unsaturated benzylidene precursor 6 were found to be the most potent (IC50 = 7 and 5 mu M, respectively), which was comparable with liarozole (7 mu M) but considerably less active than R115866 (IC50 = 5 nM). With a CYP26A1 homology model, the tetralones were shown to be positioned in a hydrophobic tunnel with additional interactions, e.g., transition metal coordination and hydrogen-bonding interactions with GLY300, observed for the potent 4-hydroxyphenyl substituted inhibitors.

  DOI：

  10.1021/jm0501681

文献信息

• Synthesis and CYP24 inhibitory activity of 2-substituted-3,4-dihydro-2H-naphthalen-1-one (tetralone) derivatives
  作者：Sook Wah Yee、Claire Simons

  DOI：10.1016/j.bmcl.2004.08.040

  日期：2004.11

  The synthesis of novel 2-benzyl- and 2-benzylidene-3,4-dihydro-2H-naphthalen-1-one (tetralone) derivatives and their inhibitory activity versus kidney mitochondrial 25-hydroxyvitamin D(3) 24-hydroxylase (CYP24) is described. The 2-benzylidenetetralone derivatives were found to be very weak inhibitors (IC(50) 20 >100 microM), whereas the 2-benzyltetralone derivatives showed promising inhibitory activity

  新型2-苄基和2-亚苄基-3,4-二氢-2H-萘-1-酮（四氢萘酮）衍生物的合成及其对肾脏线粒体25-羟基维生素D（3）24-羟化酶（CYP24）的抑制活性描述。与酮康唑相比，发现2-苄基四氢萘酮衍生物是非常弱的抑制剂（IC（50）20> 100 microM），而2-苄基四氢萘酮衍生物显示出有希望的抑制活性（活性最高的衍生物IC（50）0.9 microM）。 IC（50）20 microM）。