2-(naphthalen-1-yloxy)-1-(4-methoxyphenyl)ethan-1-one | 80554-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(naphthalen-1-yloxy)-1-(4-methoxyphenyl)ethan-1-one
• 英文别名: 1-(4-methoxyphenyl)-2-(naphthalen-1-yloxy)ethanone；1-(4-Methoxyphenyl)-2-(1-naphthyloxy)ethanone；1-(4-methoxyphenyl)-2-naphthalen-1-yloxyethanone
• CAS: 80554-47-8
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: XETJOHZWRXDDLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-1-yloxy)-1-(4-methoxyphenyl)ethan-1-one 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到(Z)-1-(4-methoxyphenyl)-2-(naphthalen-1-yloxy)ethanone oxime
  参考文献：
  名称：

  Discovery of oxime-bearing naphthalene derivatives as a novel structural type of Nrf2 activators

  摘要：

  Recent studies have demonstrated that oxidative stress insult is one of major causes of tumor formation. Therefore, identify the effective anti-oxidative agents as a preventive approach to stop cancer progression has widely explored. Although, many potent anti-oxidative ingredients in the natural products have been identified but the amount from the nature source hindrances the clinical application. Compound which can activate Nrf2 signaling pathway result unregulated the cellular antioxidant-responses has been demonstrated as an effective chemopreventive approach for cancer treatment. In the present study, certain oxime-bearing naphthalene derivatives were synthesized and evaluated for their Nrf2 activation and anti-proliferative activities. Results indicated (E)-1-(naphthalen-2-yloxy) propan-2-one oxime (11) which increased 2.04-fold Nrf2/ARE-driven luciferase activity was more active than its 1-substituted isomer 10 (1.17-fold) and t-BHQ (1.77-fold), the known Nrf2 activator. The activities were further increased by the replacement of the peripheral methyl group with the phenyl ring in which (Z)-2-(naphthalen-2-yloxy)-1-phenylethanone oxime (13a) exhibited 3.49-fold potency of the positive control. It is worth to mention that compounds 11, 13a, and 13b which showed significant Nrf2 activation are non-cytotoxic to the tested cells with IC50 > 50 mu M. This observation strongly suggested that these compounds can be used for chemoprevention. Mechanism studies indicated that these compounds were capable of inducing the phosphorylation of Nrf2 protein at serine 40 which led to the activation of the Nrf2 transcriptional activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.046
• 作为产物：
  描述：

  萘酚 、 alpha-溴-4-甲氧基苯乙酮 在 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene on polystyrene.HL 作用下， 以 丙酮 为溶剂， 生成 2-(naphthalen-1-yloxy)-1-(4-methoxyphenyl)ethan-1-one
  参考文献：
  名称：

  使用聚合物支持的试剂三步合成一系列取代的苯并呋喃

  摘要：

  通过用聚合物负载的溴化吡啶鎓过溴化物（PSPBP）将苯乙酮溴化为α-溴苯乙酮，可以实现一种有效的组合方法，以取代3-苯基苯并呋喃。随后使用1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD-P）将所得的溴化物彻底替换为苯酚，并使用Amberlyst 15将所得的α-苯氧基乙酰苯酮环化脱水，得到的纯产品不含需要任何色谱纯化步骤。

  DOI：

  10.1039/a904384e

文献信息

• Regioselective Preparation of Benzo[<i>b</i>]furans from Phenols and α<i>-</i>Bromoketones
  作者：Leire Arias、Yosu Vara、Fernando P. Cossío

  DOI：10.1021/jo201841y

  日期：2012.1.6

  In this paper, a fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted

  在本文中，描述了2-和3-取代的苯并[ b ]呋喃的完全区域控制的合成。在中性氧化铝存在下，苯酚与α-溴乙酰苯之间的直接反应生成具有完全区域控制能力的2取代的苯并[ b ]呋喃。当使用碱性盐如碳酸钾时，获得了相应的2-氧代醚。由中性氧化铝促进的这些后面化合物的环化产生相应的3-取代的苯并[ b ]呋喃。使用前一种方法，可以在两个制备步骤中从商业来源获得Moracin M和其他类似物。DFT计算提供了合理的反应路径，以了解2-取代的苯并[ b ]呋喃的形成。
• Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents
  作者：Jörg Habermann、Steven V. Ley、René Smits

  DOI：10.1039/a904384e

  日期：——

  achieved by the bromination of acetophenones to α-bromoacetophenones by polymer-supported pyridinium bromide perbromide (PSPBP). The subsequent clean substitution of the obtained bromides by phenols using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD-P) and cyclodehydration of the resulting α-phenoxyacetophenones using Amberlyst 15, affords pure products without the need for any chromatographic purification

  通过用聚合物负载的溴化吡啶鎓过溴化物（PSPBP）将苯乙酮溴化为α-溴苯乙酮，可以实现一种有效的组合方法，以取代3-苯基苯并呋喃。随后使用1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD-P）将所得的溴化物彻底替换为苯酚，并使用Amberlyst 15将所得的α-苯氧基乙酰苯酮环化脱水，得到的纯产品不含需要任何色谱纯化步骤。
• ——
  作者：Cheng-Chyi Tzeng、Kuan-Han Lee、Tai-Chi Wang、Chein-Hwa Han、Yeh-Long Chen

  DOI：10.1023/a:1007534416561

  日期：——

  Seven types of alpha-methylene-gamma-butyrolactones were evaluated in vitro against 60 human cancer cell lines derived from nine cancer cell types. The average values of log GI50 indicated that for the aryl portion, potencies of these alpha-methylene-gamma-butyrolactones are in a decreasing order of quinolin-2(1H)-one (or 2-hydroxyquinoline, 21, -5.89) > quinoline (19, -5.79) > 2-methylquinoline (20, -5

  目的本研究的主要目的是探讨γ-取代的γ-芳氧基甲基-α-亚甲基-γ-丁内酯对癌细胞的细胞毒性结构-活性关系。方法目标化合物的合成过程分为两步，首先是芳基-OH，后者是用溴甲基酮处理，然后进行Reformatsky型缩合反应。结果在体外针对来自9种癌细胞的60种人类癌细胞系评估了7种类型的α-亚甲基-γ-丁内酯。log GI50的平均值表明，对于芳基部分，这些α-亚甲基-γ-丁内酯的效能降序为quinolin-2（1H）-one（或2-hydroxyquinoline，21，-5.89）> quinoline （19，-5.79）> 2-甲基喹啉（20，-5.69）> 8-羟基喹啉（17，-5.64）> 2-萘（16，-5.59）>苯（15，-4.90）。log TGI和log LC50均获得相同的顺序。然而，对于γ-取代基，效力是联苯（16f-21f）>苯基和4-取代的苯基（16b-e-2
• Orally Administered Benzofuran Derivative Disaggregated Aβ Plaques and Oligomers in the Brain of 5XFAD Alzheimer Transgenic Mouse
  作者：DaWon Kim、Gi Hun Bae、Hye Yun Kim、Hanna Jeon、Kyeonghwan Kim、Jisu Shin、Sunhee Lee、Seungpyo Hong、Ikyon Kim、YoungSoo Kim

  DOI：10.1021/acschemneuro.0c00606

  日期：2021.1.6

  Amyloid-β (Aβ) aggregated forms are highly associated with the onset of Alzheimer’s disease (AD). Aβ abnormally accumulates in the brain and induces neuronal damages and symptoms of AD such as cognitive impairment and memory loss. Since an antibody drug, aducanumab, reduces Aβ aggregates and delays clinical decline, clearance of accumulated Aβ in the brain is accounted as a therapeutic approach to

  淀粉样蛋白-β (Aβ) 聚集形式与阿尔茨海默病 (AD) 的发病高度相关。Aβ 异常积聚在大脑中并诱导神经元损伤和 AD 症状，例如认知障碍和记忆力减退。由于抗体药物 aducanumab 可减少 Aβ 聚集并延缓临床衰退，因此清除大脑中积累的 Aβ 被认为是治疗 AD 的一种治疗方法。在这项研究中，我们合成了 17 种苯并呋喃衍生物，它们可以将 Aβ 低聚物和斑块分解成惰性单体。通过一系列利用硫黄素 T 测定和凝胶电泳的 Aβ 聚集抑制和聚集体解聚测定，YB-9，2-((5-甲氧基-3-(4-甲氧基苯基)苯并呋喃-6-基)氧基)乙酸被选为最终的Aβ-解聚剂候选者。8个月大的具有5个家族性AD突变（5XFAD）的雄性转基因小鼠模型每天通过饮用水口服给药两个月，海马中的Aβ寡聚体和斑块减少。因此，与未处理的转基因对照组相比，在YB-9处理的 5XFAD 小鼠的海马中观察到星形胶质细胞增生减少和突触功能障碍得到恢复。
• BCl3-promoted synthesis of benzofurans
  作者：Ikyon Kim、Sei-Hee Lee、Sunkyung Lee

  DOI：10.1016/j.tetlet.2008.09.034

  日期：2008.11

  Lewis acidic nature of boron trichloride (BCl3) to coordinate to the carbonyl functionality was exploited for the synthesis of benzofurans via dehydrative cyclization. This mild and efficient procedure allowed for facile access to a number Of highly Substituted benzofurans in a regioselective manner. The Structural requirement for the successful cyclodehydration was examined in the cases, where competitive demethylation could occur. (C) 2008 Elsevier Ltd. All rights reserved.