5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol
• 英文别名: 5-(6-hydroxynaphthalen-2-yl)benzene-1,2,3-triol
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: PBTSXIZGBMXUHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 碘 、 三溴化硼 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol
  参考文献：
  名称：

  Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase

  摘要：

  Oxyresveratrol and resveratrol, with hydroxy substituted trans-stilbene structure, exert potent inhibitory effects on cyclooxygenase, rat liver mitochondrial ATPase activity, and tyrosinase. As the isosteres of oxyresveratrol, a new family of hydroxyl substituted phenyl-naphthalenes were synthesized to show excellent inhibition of mushroom tyrosinase. Compound 10, which is isostere of resveratrol, showed IC50 value of 16.52 mu M in mushroom tyrosinase activity. As compared to this, the reference compound, resveratrol, showed IC50 value of 55.61 mu M. Compound 4, which is isostere of oxyresveratrol, showed IC50 value of 0.49 mu M. Among the other three derivatives, compound 13 showed IC50 value of 0.034 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.025
• 作为试剂：
  描述：

  L-酪氨酸 在 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol 、 mushroom monophenol monooxygenase EC 1.14.18.1 作用下， 以 水 为溶剂， 生成 多巴醌硫酸盐
  参考文献：
  名称：

  A newly synthesized, potent tyrosinase inhibitor: 5-(6-Hydroxy-2-naphthyl)-1,2,3-benzenetriol

  摘要：

  In searching for new agents with a depigmenting effect, we synthesized a derivative of resveratrol, 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol ( 5HNB) with a potent tyrosinase inhibitory activity. 5HNB inhibited mushroom tyrosinase with an IC(50) value of 2.95 mu M, which is more potent than the well-known anti-tyrosinase activity of kojic acid (IC(50) = 38.24). The results of the enzymatic inhibition kinetics by Lineweaver-Burk analysis indicated 5HNB inhibits tyrosinase non-competitively when L-tyrosine was used as the substrate. Based on the strong inhibitory action of 5HNB, it is expected that 5HNB can suppress melanin production in which tyrosinase plays the essential role. Our expectation was confirmed by the experimentations with B16 melanoma cells in which 5HNB inhibited melanin production. We propose that 5HNB might have skin-whitening effects as well as therapeutic potential for treating skin pigmentation disorders. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.087

文献信息

• Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase
  作者：Suhee Song、Hyojin Lee、Youngeup Jin、Young Mi Ha、Sungjin Bae、Hae Young Chung、Hongsuk Suh

  DOI：10.1016/j.bmcl.2006.10.025

  日期：2007.1

  Oxyresveratrol and resveratrol, with hydroxy substituted trans-stilbene structure, exert potent inhibitory effects on cyclooxygenase, rat liver mitochondrial ATPase activity, and tyrosinase. As the isosteres of oxyresveratrol, a new family of hydroxyl substituted phenyl-naphthalenes were synthesized to show excellent inhibition of mushroom tyrosinase. Compound 10, which is isostere of resveratrol, showed IC50 value of 16.52 mu M in mushroom tyrosinase activity. As compared to this, the reference compound, resveratrol, showed IC50 value of 55.61 mu M. Compound 4, which is isostere of oxyresveratrol, showed IC50 value of 0.49 mu M. Among the other three derivatives, compound 13 showed IC50 value of 0.034 mu M. (c) 2006 Elsevier Ltd. All rights reserved.