1-(4-bromophenyl)-2-(naphthalen-2-yloxy)ethanone | 25789-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-bromophenyl)-2-(naphthalen-2-yloxy)ethanone
• 英文别名: β-Naphthol-p-bromphenacylether；1-(4-Bromophenyl)-2-naphthalen-2-yloxyethanone
• CAS: 25789-36-0
• 化学式: C₁₈H₁₃BrO₂
• 分子量: 341.204
• InChiKey: UXFUBINLFLWBFP-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  503.4±35.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-2-(naphthalen-2-yloxy)ethanone 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以60%的产率得到(Z)-1-(4-bromophenyl)-2-(naphthalen-2-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：

  2,4'-二溴苯乙酮 、 2-萘酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81 %的产率得到1-(4-bromophenyl)-2-(naphthalen-2-yloxy)ethanone
  参考文献：
  名称：

  呋喃喹啉氮杂螺烯的结构和光物理性质：质子化增强荧光

  摘要：

  近年来，在聚芳族主链中引入一个或多个杂芳环引起了越来越多的兴趣，因为它可以显着控制光学、电子和超分子特性。多杂芳族化合物由于其光和电化学性质而成为潜在的光电共轭材料。这项工作描述了由容易获得的起始化合物合成的呋喃喹啉系列氮杂氧螺旋烯的第一个代表的结构和光物理性质。使用X射线衍射分析和DFT计算，确定呋喃稠合的氮杂[5]螺旋烯与其碳类似物不同，由于末端碳原子之间的距离增加而不会发生马洛里型光环化，这决定了它们对紫外线的抵抗力更强。对所得化合物的酸致变色特性的研究表明，三氟乙酸（TFA）的质子化导致大多数荧光团的荧光强度增加。外围苯基部分含有甲氧基取代基的荧光团获得了最好的荧光增强，量子产率增加了 10 倍。将呋喃喹啉残基引入螺旋烯骨架中可以改善荧光特性，以及通过酸性剂调节荧光特性的可能性。未来，萘并呋喃喹啉系列氮杂氧十六烯的首批代表将用于设计光电新材料并研究其性能特性。

  DOI：

  10.1016/j.dyepig.2024.112032

文献信息

• Synthesis and structure–activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain
  作者：José Wanderlan Pontes Espíndola、Marcos Veríssimo de Oliveira Cardoso、Gevanio Bezerra de Oliveira Filho、Dayane Albuquerque Oliveira e Silva、Diogo Rodrigo Magalhaes Moreira、Tanira Matutino Bastos、Carlos Alberto de Simone、Milena Botelho Pereira Soares、Filipe Silva Villela、Rafaela Salgado Ferreira、Maria Carolina Accioly Brelaz de Castro、Valéria Rego Alves Pereira、Silvane Maria Fonseca Murta、Policarpo Ademar Sales Junior、Alvaro José Romanha、Ana Cristina Lima Leite

  DOI：10.1016/j.ejmech.2015.06.048

  日期：2015.8

  thiosemicarbazone-based conformationally constrained analogs of thiosemicarbazones (1) and (2) were developed as potential inhibitors of the T. cruzi protease cruzain, using a rigidification strategy of the iminic bond of (1) and (2). A structure–activity relationship analysis was performed in substituents attached in both aryl and aryloxy rings. This study indicated that apolar substituents or halogen atom substitution

  有必要发现一种新的抗查加斯锥虫病的病原体克氏锥虫的抗寄生虫化合物。新颖的芳氧基芳基缩氨基硫脲基构象受限缩氨基硫脲（类似物/ 1）和（2）被开发作为潜在抑制剂的锥虫蛋白酶cruzain，使用的（在iminic键的硬化策略1）和（2）。结构-活性关系分析是在芳基和芳氧基环上连接的取代基上进行的。这项研究表明，与未取代的硫代半脲相比，芳基位置的非极性取代基或卤素原子取代改善了Cruzain的抑制作用和抗寄生虫活性。这些化合物中的两种通过抑制Cruzain表现出有效的抑制性抗寄生虫活性，因此能够减少感染细胞中的寄生虫负担，并通过坏死导致寄生虫细胞死亡。总之，我们证明了构象限制是开发抗寄生虫硫代氨基脲的有价值的策略。
• Thorat, M. T.; Mane, R. B.; Jagdale, M. H., Journal of the Indian Chemical Society, 1987, vol. 64, # 2, p. 106 - 107
  作者：Thorat, M. T.、Mane, R. B.、Jagdale, M. H.、Salunkhe, M. M.

  DOI：——

  日期：——
• THORAT, M. T.;MANE, R. B.;JAGDALE, M. H.;SALUNKHE, M. M., J. INDIAN CHEM. SOC., 64,(1987) N 2, 106-107
  作者：THORAT, M. T.、MANE, R. B.、JAGDALE, M. H.、SALUNKHE, M. M.

  DOI：——

  日期：——
• US4111962A
  申请人：——

  公开号：US4111962A

  公开（公告）日：1978-09-05
• Photophysics of Luminescent Azahelicenes of the Furoquinoline Series
  作者：V. S. Tamozhnikova、V. V. Semionova、V. P. Grivin、E. M. Glebov、R. Yu. Balakhonov、I. S. Mekeda、V. Z. Shirinian

  DOI：10.1134/s0018143923090175

  日期：2023.12