2-(3,5-dimethoxyphenyl)-6-methoxy naphthalene | 869788-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3,5-dimethoxyphenyl)-6-methoxy naphthalene
• 英文别名: 2-(3,5-dimethoxyphenyl)-6-methoxy-naphthalene；2-(3,5-Dimethoxy-phenyl)-6-methoxy-naphthalene；2-(3,5-dimethoxyphenyl)-6-methoxynaphthalene
• CAS: 869788-93-2
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: FMOKYAYPFVBPIG-UHFFFAOYSA-N

物化性质

• 熔点：
  90-93 °C
• 沸点：
  444.2±35.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethoxyphenyl)-6-methoxy naphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以93%的产率得到5-(6-Hydroxy-naphthalen-2-yl)-benzene-1,3-diol
  参考文献：
  名称：

  Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells

  摘要：

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.

  DOI：

  10.1021/jm060253o
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 2-(3,5-dimethoxyphenyl)-6-methoxy naphthalene
  参考文献：
  名称：

  Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells

  摘要：

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.

  DOI：

  10.1021/jm060253o

文献信息

• Resorcinarene-mono-benzimidazolium salts as NHC ligands for Suzuki--Miyaura cross-couplings catalysts
  作者：Ümit İŞCİ、Muhittin AYGÜN、Resul SEVİNCEK、Yunus ZORLU、Fabienne DUMOULİN

  DOI：10.3906/kim-1506-50

  日期：——

  Two mono-benzimidazolium salts of resorcinarene have been prepared and used as ligands in Suzuki--Miyaura cross-coupling reactions. They have been fully characterized by $^1}$H and $^13}$C NMR, MALDI, and FT-IR spectroscopic methods, and their structures were confirmed by X-ray diffraction analysis. These two new resorcinarene-based mono-benzimidazolium salts showed good catalytic activity for coupling reactions in DMF. The highest conversion was achieved for arylation of 4-bromotoluene using the resorcinarenyl mono-dimethylbenzimidazolium salt.

  已经制备了两种基于重氮树脂的单苯并咪唑盐，并作为配体用于铃木-宫浦交叉偶联反应。它们通过 $^1}$H 和 $^13}$C NMR、MALDI 和 FT-IR 光谱方法进行了全面表征，并通过 X 射线衍射分析确认了其结构。这两种新的基于重氮树脂的单苯并咪唑盐在 DMF 中对偶联反应表现出良好的催化活性。使用重氮树脂单二甲基苯并咪唑盐对 4-溴甲苯进行芳基化反应时，达到了最高转化率。
• Synthesis of a Resveratrol Analogue with High Ceramide-Mediated Proapoptotic Activity on Human Breast Cancer Cells
  作者：Filippo Minutolo、Giusy Sala、Annalisa Bagnacani、Simone Bertini、Isabella Carboni、Giorgio Placanica、Giovanni Prota、Simona Rapposelli、Nicoletta Sacchi、Marco Macchia、Riccardo Ghidoni

  DOI：10.1021/jm050528k

  日期：2005.11.1

  Resveratrol, a natural product with a stilbene structure, exerts profound proapoptotic activity in human cancer cells, by triggering the accumulation of ceramide, a bioactive sphingolipid. We studied the biological effects of seven methoxylated and/or naphthalene-based resveratrol analogues and compared these compounds with resveratrol with the objective to identify an analogue with higher ceramide-mediated proapoptotic activity relative to resveratrol. Here we show that the compound with three hydroxyls and a naphthalene ring is the most effective in triggering apoptosis coupled to the induction of endogenous ceramide in human cancer cells.
• 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.
• A newly synthesized, potent tyrosinase inhibitor: 5-(6-Hydroxy-2-naphthyl)-1,2,3-benzenetriol
  作者：Jehun Choi、Sung Jin Bae、Young Mi Ha、Jae Kyung No、Eun Kyeong Lee、Jun Sik Lee、Suhee Song、Hyojin Lee、Hongsuk Suh、Byung Pal Yu、Hae Young Chung

  DOI：10.1016/j.bmcl.2010.06.087

  日期：2010.8

  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.
• Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells
  作者：Marinella Roberti、Daniela Pizzirani、Maurizio Recanatini、Daniele Simoni、Stefania Grimaudo、Di Cristina、Vincenzo Abbadessa、Nicola Gebbia、Manlio Tolomeo

  DOI：10.1021/jm060253o

  日期：2006.5.1

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.