4-(6-hydroxy-2-naphthyl)-1,3-benzenediol | 927885-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(6-hydroxy-2-naphthyl)-1,3-benzenediol
• 英文别名: 4-(6-Hydroxynaphthalen-2-yl)benzene-1,3-diol
• CAS: 927885-00-5
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: BXZJBSHLEZAMOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 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：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

制备方法与用途

HS-1793是一种白藜芦醇类似物，在多种癌细胞系中表现出抗肿瘤活性。研究显示，HS-1793能够诱导细胞凋亡。

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 4-(6-hydroxy-2-naphthyl)-1,3-benzenediol
  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

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.