1-(4-ethoxy-1-hydroxynaphthalen-2-yl)ethan-1-one | 288074-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-ethoxy-1-hydroxynaphthalen-2-yl)ethan-1-one
• 英文别名: 4'-ethoxy-1'-hydroxy-2'-acetonaphthone；2-acetyl-4-ethoxy-1-naphthol；1-(4-Ethoxy-1-hydroxynaphthalen-2-yl)ethanone
• CAS: 288074-67-9
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: RCJFKDMFPZLNLO-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C
• 沸点：
  390.3±22.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-ethoxy-1-hydroxynaphthalen-2-yl)ethan-1-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 生成 1-(5-hydroxy-2-methoxy-2-methyl-2,3-dihydronaphtho[1,2-b]furan-4-yl)ethanone
  参考文献：
  名称：

  Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans

  摘要：

  Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 21 cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using L-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia colt (KTC-1924) and gram-positive Staphylococcus aureus (KTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 = 8.91 mu g/mL), which was comparable with that of standard kojic acid (IC50 = 10.16 mu g/ mL), potent antioxidant activity (IC50 = 3.33 mu g/mL), which was comparable with that of BHT (IC50 = 34.67 mu g/mL), and excellent antibacterial activities (MICs: 0.50 mu g/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 mu g/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 mu g/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 mu g/mL, which was comparable to that of ampicillin (MIC = 0.5 mu g/mL). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.025
• 作为产物：
  描述：

  1,4-二羟基萘 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-(4-ethoxy-1-hydroxynaphthalen-2-yl)ethan-1-one
  参考文献：
  名称：

  Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans

  摘要：

  Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 21 cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using L-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia colt (KTC-1924) and gram-positive Staphylococcus aureus (KTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 = 8.91 mu g/mL), which was comparable with that of standard kojic acid (IC50 = 10.16 mu g/ mL), potent antioxidant activity (IC50 = 3.33 mu g/mL), which was comparable with that of BHT (IC50 = 34.67 mu g/mL), and excellent antibacterial activities (MICs: 0.50 mu g/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 mu g/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 mu g/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 mu g/mL, which was comparable to that of ampicillin (MIC = 0.5 mu g/mL). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.025

文献信息

• Synthetic Utility and Mechanistic Implications of the Fries Rearrangement of Hydroquinone Diesters in Boron Trifluoride Complexes
  作者：Jessica L. Boyer、Jodie E. Krum、Michael C. Myers、Aleem N. Fazal、Carl T. Wigal

  DOI：10.1021/jo000412q

  日期：2000.7.1

  trifluoride etherate complexes results in acetylhydroquinone derivatives. This procedure represents a one-step synthesis of acetylhydroquinone derivatives, important building blocks for a variety of synthetic applications.

  三氟化硼甲基和乙基醚化物配合物与对苯二酚二酯的反应可生成乙酰氢醌的单甲基和单乙基衍生物。使用位阻三氟化硼醚化物配合物会生成乙酰氢醌衍生物。该步骤代表一步合成乙酰氢醌衍生物，这是各种合成应用的重要组成部分。
• Benzoflavone activators of the cystic fibrosis transmembrane conductance regulator: towards a pharmacophore model for the nucleotide-binding domain
  作者：Mark F Springsteel、Luis J.V Galietta、Tonghui Ma、Kolbot By、Gideon O Berger、Hong Yang、Christopher W Dicus、Wonken Choung、Chao Quan、Anang A Shelat、R.Kiplin Guy、A.S Verkman、Mark J Kurth、Michael H Nantz

  DOI：10.1016/s0968-0896(03)00435-8

  日期：2003.9

  using cell-based assays, of a series of benzoflavone analogues to examine structure-activity relationships and to identify compounds having greater potency for activation of both wild type CFTR and a mutant CFTR (G551D-CFTR) that causes cystic fibrosis in some human subjects. Using UCCF-029 as a structural guide, a panel of 77 flavonoid analogues was prepared. Analysis of the panel in FRT cells indicated

  我们以前对黄酮类化合物和相关杂环的筛选具有激活囊性纤维化跨膜电导调节剂（CFTR）氯化物通道的能力，这表明UCCF-029是一种7,8-苯并黄酮，是一种有效的活化剂。在本研究中，我们描述了使用基于细胞的分析方法对一系列苯并黄酮类似物进行合成和评估，以检查其结构活性关系，并鉴定出对野生型CFTR和突变型CFTR（G551D -CFTR）在某些人类受试者中引起囊性纤维化。使用UCCF-029作为结构指导，制备了77种类黄酮类似物。对FRT细胞中面板的分析表明，黄酮A环在7,8位的苯环显着提高了化合物活性和几种类黄酮的效力。在3或4位上引入B环吡啶基氮也可提高CFTR活性，但这种结构修饰的影响不如苯甲环化均匀。最有效的新类似物UCCF-339以1.7 microM的K（d）激活了野生型CFTR，它比以前最有效的CFTR类黄酮活化剂芹菜素具有更高的活性。苯并黄酮类化合物中的几种化合物也可以活化G5
• Anti-tyrosinase, antioxidant, and antibacterial activities of novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans
  作者：Likai Xia、Akber Idhayadhulla、Yong Rok Lee、Young-Jung Wee、Sung Hong Kim

  DOI：10.1016/j.ejmech.2014.09.025

  日期：2014.10

  Novel 5-hydroxy-4-acetyl-2,3-dihydronaphtho[1,2-b]furans (7a-k) were synthesized using ceric ammonium nitrate (CAN)-catalyzed formal [3 + 21 cycloaddition. Synthesized compounds were evaluated for their tyrosinase inhibitory, antioxidant, and antibacterial activities. A modified spectrophotometric method using L-DOPA as substrate was used to determine tyrosinase inhibitory activities, and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay was used to evaluate antioxidant properties. Antibacterial activities against gram-negative Escherichia colt (KTC-1924) and gram-positive Staphylococcus aureus (KTC-1916) were evaluated using the disc diffusion technique. Of the synthesized compounds, 7b with a 4-acetyl and an electron-enriched dihydronaphthofuran ring showed the highest tyrosinase-inhibition activity (IC50 = 8.91 mu g/mL), which was comparable with that of standard kojic acid (IC50 = 10.16 mu g/ mL), potent antioxidant activity (IC50 = 3.33 mu g/mL), which was comparable with that of BHT (IC50 = 34.67 mu g/mL), and excellent antibacterial activities (MICs: 0.50 mu g/mL against E. coli and S. aureus strains). A mechanistic analysis of 7b demonstrated that its tyrosinase inhibitory activity was reversible and competitive. Compounds 7c and 7d showed potent antioxidant activities (IC50: 6.30 and 5.01 mu g/mL), and compound 7d also exhibited potent inhibitory activity against E. coli with a MIC of 0.5 mu g/mL. Furthermore, compounds 7a, 7e, 7f, and 7i showed potent antibacterial activities against S. aureus with MICs of 0.5 mu g/mL, which was comparable to that of ampicillin (MIC = 0.5 mu g/mL). (C) 2014 Elsevier Masson SAS. All rights reserved.