(E)-1-(4'-methoxyphenyl)-3-(naphthalen-1''-yl)prop-2-en-1-one | 56412-54-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4'-methoxyphenyl)-3-(naphthalen-1''-yl)prop-2-en-1-one
• 英文别名: (E)-1-(4-methoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one；(2E)-1-(4'-methoxyphenyl)-3-(1-naphthyl)-2-propen-1-one；1-(4-Methoxyphenyl)-3-(1-naphthyl)prop-2-en-1-one；(E)-1-(4-methoxyphenyl)-3-naphthalen-1-ylprop-2-en-1-one
• CAS: 56412-54-5
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: QUCMFZOJKRASJO-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  氨基硫脲 、 (E)-1-(4'-methoxyphenyl)-3-(naphthalen-1''-yl)prop-2-en-1-one 以 乙醇 为溶剂， 反应 5.0h， 以79%的产率得到3-(4-methoxyphenyl)-5-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazole-1-thioamide
  参考文献：
  名称：

  Design, modification and 3D QSAR studies of novel naphthalin-containing pyrazoline derivatives with/without thiourea skeleton as anticancer agents

  摘要：

  Two series of novel naphthalin-containing pyrazoline derivatives C1-C14 and D1-D14 have been synthesized and evaluated for their EGFR/HER-2 inhibitory and anti-proliferation activities. Compound D14 displayed the most potent activity against EGFR and A549 cell line (IC50 = 0.05 mu M and GI(50) = 0.11 mu M), being comparable with the positive control Erlotinib (IC50 = 0.03 mu M and GI(50) = 0.03 mu M) and more potent than our previous compounds C0-A (IC50 = 5.31 mu M and GI(50) = 33.47 mu M) and C0-B (IC50 = 0.09 mu M and GI(50) = 0.34 mu M). Meanwhile, compound C14 displayed the most potent activity against HER-2 and MCF-7 cell line (IC50 = 0.88 mu M and GI(50) = 0.35 mu M), being a little less potent than Erlotinib (IC50 = 0.16 mu M and GI(50) = 0.08 mu M) but far more potent than C0-A (IC50 = 6.58 mu M and GI(50) = 27.62 mu M) and C0-B (IC50 = 2.77 mu M and GI(50) = 3.79 mu M). The docking simulation was performed to analyze the probable binding models and the QSAR models were built for reasonable design of EGFR/HER-2 inhibitors at present and in future. The structural modification of introducing naphthalin moiety reinforced the combination of our compounds and the receptor, resulting in progress of bioactivity. Moreover, the replacement of thiourea skeleton by using benzene ring resulted in the slight diversity of the two series towards specific targets. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.013
• 作为产物：
  描述：

  (E)-3-(naphthalen-1-yl)acrylic acid 在 N-甲基吗啉 、 palladium diacetate 、 正丁基二(1-金刚烷基)膦 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 (E)-1-(4'-methoxyphenyl)-3-(naphthalen-1''-yl)prop-2-en-1-one
  参考文献：
  名称：

  钯催化的 α,β-不饱和超活性三嗪酯的 Suzuki-Miyaura 偶联

  摘要：

  钯催化的 α,β-不饱和酸衍生物的 Suzuki-Miyaura 偶联具有挑战性，因为它们的 C C 键与羰基相邻。在这项工作中，我们描述了一种使用超活性三嗪酯和有机硼作为偶联伙伴来实现这种转化的高选择性 C-O 活化方法。用该方法制备了 42 种具有不同官能团的 α,β-不饱和酮。机理研究表明，三嗪激活 C-O 键和稳定催化剂与底物之间的非共价相互作用的双重功能对于反应的成功至关重要。该方法的效率、功能组兼容性和独特的机制使其成为经典方法的有价值的替代品。

  DOI：

  10.1039/d3cc00336a

文献信息

• Alkene Synthesis by Photo‐Wolff‐Kischner Reaction of Sulfur Ylides and <i>N</i> ‐Tosylhydrazones
  作者：Pan‐Pan Gao、Dong‐Mei Yan、Ming‐Hang Bi、Min Jiang、Wen‐Jing Xiao、Jia‐Rong Chen

  DOI：10.1002/chem.202102671

  日期：2021.10.13

  A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity

  首次开发了硫叶立德和 N-甲苯磺酰腙的可见光驱动和室温光沃尔夫-基施纳反应，以提供烯烃合成的模块化途径。60 多个实例证明了高官能团耐受性和广泛的底物范围。产品中的 E- 和 Z- 烯烃立体化学都可以以优异的立体选择性进行控制。一系列机理研究支持该反应应该通过自由基 - 负离子交叉途径进行，具体涉及将光生硫叶立德自由基阳离子添加到 N-甲苯磺酰腙形成碳负离子和随后的沃尔夫-基施纳过程。
• Visible Light Activated Radical Denitrative Benzoylation of<i>β</i>-Nitrostyrenes: A Photocatalytic Approach to Chalcones
  作者：Shubhangi Tripathi、Ritu Kapoor、Lal Dhar S. Yadav

  DOI：10.1002/adsc.201701559

  日期：2018.4.3

  A metal‐free, convenient photocatalytic approach to chalcones from β‐nitrostyrenes and benzaldehydes via a radical denitrative benzoylation pathway is reported. The salient features of the protocol include the utilization of visible light as an inexpensive and ecosustainable energy source, N‐hydroxyphthalimide (NHPI) as a reusable organophotocatalyst and acetonitrile as an acceptable green solvent

  据报道，一种无金属，方便的光催化方法可通过自由基反硝化苯甲酰化途径从β-硝基苯乙烯和苯甲醛中分离出查耳酮。该协议的显着特征包括利用可见光作为一种廉价且生态可持续的能源，使用N-羟基邻苯二甲酰亚胺（NHPI）作为可重复使用的有机光催化剂，使用乙腈作为一种可接受的绿色溶剂，以在室温下以优异的产率提供查耳酮。锅程序。值得注意的是，这是β-硝基苯乙烯作为查尔酮合成的现成底物的首次应用，也是该领域中光催化的第一个实例。
• Synthesis of chalcone derivatives by Claisen-Schmidt condensation and <i>in vitro</i> analyses of their antiprotozoal activities
  作者：Gabriella B. Souza、Tamiris A. C. Santos、Amanda P. S. Silva、André L. B. S Barreiros、Victória Brandão Nardelli、Ingrid B. Siqueira、Silvio S. Dolabella、Emmanoel.V. Costa、Péricles B. Alves、Ricardo Scher、Roberta P. M. Fernandes

  DOI：10.1080/14786419.2022.2140337

  日期：——

  Chalcone is a molecule with known biological activities. Based on this, a series of chalcone derivatives bearing methyl, phenyl or furanyl substituents at different positions of A and B rings were ...

  查耳酮是一种具有已知生物活性的分子。在此基础上，合成了一系列A、B环不同位置带有甲基、苯基或呋喃基取代基的查尔酮衍生物...
• Carbonylative Heck Reactions Using CO Generated <i>ex Situ</i> in a Two-Chamber System
  作者：Philippe Hermange、Thomas M. Gøgsig、Anders T. Lindhardt、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1021/ol200686h

  日期：2011.5.6

  A carbonylative Heck reaction of aryl iodides and styrene derivatives employing a two-chamber system using a stable, crystalline, and nontransition metal based carbon monoxide source is reported. By applying near-stoichiometric amounts of the carbon monoxide precursor, an effective exploitation of the hazardous CO gas is obtained affording chalcone derivatives in good yields. Application to isotope labeling, incorporating (13)CO, was further established.
• Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
  作者：Louise Domeneghini Chiaradia、Alessandra Mascarello、Marcela Purificação、Javier Vernal、Marlon Norberto Sechini Cordeiro、María Emilia Zenteno、Andréa Villarino、Ricardo José Nunes、Rosendo Augusto Yunes、Hernán Terenzi

  DOI：10.1016/j.bmcl.2008.09.105

  日期：2008.12

  In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were obtained by aldolic condensation between aldehydes and acetophenones, under basic conditions. Five compounds presented moderate or good activity. The structure - activity analysis reveals that the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents. (C) 2008 Elsevier Ltd. All rights reserved.