2-[(3'-fluorophenyl)amine]-1,4-naphthalenedione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[(3'-fluorophenyl)amine]-1,4-naphthalenedione
• 英文别名: 2-(3-fluoroanilino)-1,4-naphthoquinone；2-(3-Fluorophenylamino)-1,4-naphthoquinone；2-(3-fluoroanilino)naphthalene-1,4-dione
• 化学式: C₁₆H₁₀FNO₂
• 分子量: 267.259
• InChiKey: XCGWVHAZJLTYIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  zinc trifluoromethanesulfonate 、 2-[(3'-fluorophenyl)amine]-1,4-naphthalenedione 在 叔丁基过氧化氢 、 ferrous(II) sulfate heptahydrate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 以76%的产率得到2-[(3-fluorophenyl)amino]-3-trifluoromethyl-1,4-naphthoquinone
  参考文献：
  名称：

  C–H Trifluoromethylation of 2-Substituted/Unsubstituted Aminonaphthoquinones at Room Temperature with Bench-Stable (CF₃SO₂)₂Zn: Synthesis and Antiproliferative Evaluation

  摘要：

  A direct C-H trifluoromethylation of 2-amino1,4-naphthoquinone analogues is described. This reaction proceeds under mild conditions at open atmosphere, providing a range of CF3-containing naphthoquinones with good yield and functional group compatibility. All synthetic compounds were screened for antiproliferative activity against three human cancer cell lines. Notably, some of those trifluoromethyl analogs, such as 3a, 3g, 3j, and 3t, showed good antiproliferative profiles.

  DOI：

  10.1021/acs.joc.7b00940
• 作为产物：
  描述：

  3-氟苯胺 、 1,4-萘醌 在 copper(II) acetate monohydrate 、 溶剂黄146 作用下， 生成 2-[(3'-fluorophenyl)amine]-1,4-naphthalenedione
  参考文献：
  名称：

  通过CH官能化合成新型取代的甲氧基苯并[2,3- b ]咔唑衍生物。其光物理性质的实验和理论表征

  摘要：

  通过苯胺与萘醌的氧化偶合，然后钯催化的氧化C H官能化和一锅还原甲基化反应，制备了新颖的高蓝色荧光N-甲基-6,11-二甲氧基苯并[2,3- b ]咔唑衍生物。对苯并咔唑荧光团进行了光物理表征，并研究了取代基的作用。（TD）-DFT计算忠实地再现了苯并咔唑的实验光物理性质，并揭示了取代基如何影响这些化合物的光物理性质。

  DOI：

  10.1016/j.dyepig.2016.08.012

文献信息

• Synthesis of novel substituted methoxybenzo[2,3-b]carbazole derivatives via C-H functionalization. Experimental and theoretical characterization of their photophysical properties
  作者：Cinthia da Silva Lisboa、Nanci C. de Lucas、Simon J. Garden

  DOI：10.1016/j.dyepig.2016.08.012

  日期：2016.11

  3-b]carbazole derivatives were prepared by oxidative coupling of anilines with naphthoquinone followed by palladium catalyzed oxidative CH functionalization and a one pot reductive methylation reaction. The benzocarbazole fluorophores were photophysically characterized and the effects of the substituents investigated. (TD)-DFT calculations faithfully reproduced experimental photophysical properties of the

  通过苯胺与萘醌的氧化偶合，然后钯催化的氧化C H官能化和一锅还原甲基化反应，制备了新颖的高蓝色荧光N-甲基-6,11-二甲氧基苯并[2,3- b ]咔唑衍生物。对苯并咔唑荧光团进行了光物理表征，并研究了取代基的作用。（TD）-DFT计算忠实地再现了苯并咔唑的实验光物理性质，并揭示了取代基如何影响这些化合物的光物理性质。
• An Experimental and Theoretical Study of the Substituent Effects on the Redox Properties of 2-[(R-phenyl)amine]-1,4-naphthalenediones in Acetonitrile
  作者：M. Aguilar-Martínez、G. Cuevas、M. Jiménez-Estrada、I. González、B. Lotina-Hennsen、N. Macías-Ruvalcaba

  DOI：10.1021/jo990186o

  日期：1999.5.1

  exhibit two, one-electron reduction waves corresponding to the formation of radical-anion and dianion, where the half-wave potential values vary linearly with the Hammett constants (sigma(x)). The analysis of the different voltammetric parameters (e.g., voltammetric function, anodic/cathodic peak currents ratio, and the separation between the anodic and cathodic potential peaks) show that with the

  我们合成并分析了19种3'-（间-）和4'-（对-）取代的2-[（（R-苯基）胺] -1,4-萘二酮（PANs））化合物R = p-MeO，p- Me，p-Bu，p-Hex，p-Et，m-Me，m-Et，H，p-Cl，p-Br，mF，m-Cl，p-COCH（3），m-CN，m -NO（2），m-COOH和p-COOH。尽管将醌与间位和对位取代的环结合的氮原子会干扰两个环之间的直接共轭，但这些化合物的UV-vis光谱显示，存在着各自分子内的分子内电子转移苯胺到对萘醌部分。根据该供体-受体的特性，这些化合物的循环伏安图显示出两个单电子还原波，分别对应于自由基阴离子和二价阴离子的形成，半波电势值随Hammett常数（sigma（x））线性变化。对不同伏安参数（例如，伏安函数，阳极/阴极峰电流之比以及阳极和阴极电势峰之间的分离）的分析显示，除羧基PAN衍生物外，所有化合物均呈现相同的还原途径。我们
• 2-(Fluoro-) and 2-(methoxyanilino)-1,4-naphthoquinones. Synthesis and mechanism and effect of fluorine substitution on redox reactivity and NMR
  作者：Elisa Leyva、Kim M. Baines、Claudia G. Espinosa-González、Diego A. Magaldi-Lara、Silvia E. Loredo-Carrillo、Telma A. De Luna-Méndez、Lluvia I. López

  DOI：10.1016/j.jfluchem.2015.08.016

  日期：2015.12

  addition of methoxy- and fluoroanilines with 1,4-naphthoquinone to give methoxy- and fluoro-substituted 2-(anilino)-1,4-naphthoquinones was investigated. In the absence of a catalyst, this reaction requires long times and low yields of the anilino derivatives are obtained accompanied with the formation of several secondary products. Excellent yields were obtained with a catalytic amount of a Lewis acid

  研究了催化剂对1,4-萘醌加甲氧基和氟苯胺生成甲氧基和氟取代的2-（苯胺基）-1,4-萘醌的影响。在没有催化剂的情况下，该反应需要长时间并且获得低产率的苯胺基衍生物，并伴随着几种副产物的形成。用催化量的具有强氧化性能的路易斯酸（例如CeCl 3或FeCl 3）获得了优异的收率。当用布朗斯台德酸/氧化剂混合物例如AcOH / Cu（OAc）2进行反应时，也获得了优异的产率。还使用微波辐射研究了该加成反应。讨论了反应条件和机理。这使用二维1 H– 13 C gHSQC和gHMBC NMR实验分析并分配了所有衍生物的1 H和13 C NMR数据。还研究了氟取代对氧化还原和NMR性能的影响。
• Synthesis, spectral and electrochemical characterization of novel 2-(fluoroanilino)-1,4-naphthoquinones
  作者：Elisa Leyva、Lluvia I. López、Silvia E. Loredo-Carrillo、Margarita Rodríguez-Kessler、Antonio Montes-Rojas

  DOI：10.1016/j.jfluchem.2010.12.001

  日期：2011.2

  The preparation of novel 2-(fluoroanilino)-1,4-naphthoquinones is presented. It takes place under mild conditions by reacting the corresponding fluoroaniline and 1,4-naphthoquinone in the presence of a Lewis acid catalyst with strong oxidation properties such as CeCl3·7H2O. This preparation was also investigated under microwave irradiation. All 1,4-naphthoquinone derivatives were characterized by UV–Vis

  介绍了新型2-（氟苯胺基）-1,4-萘醌的制备。它是在温和的条件下，通过使相应的氟苯胺和1,4-萘醌在具有强氧化性能的路易斯酸催化剂（例如CeCl 3 ·7H 2 O）存在下反应来进行的。该制备方法也在微波辐射下进行了研究。所有1，4-萘醌衍生物均通过UV-Vis，IR，1 H和19 F NMR，MS和循环伏安法进行表征，以研究含氟取代基对其电子性能的影响。
• Novel 2-Amino-1,4-Naphthoquinone Derivatives Induce A549 Cell Death through Autophagy
  作者：Hua-Yuan Tan、Feng-Ming Liang、Wen-Jing Zhang、Yi Zhang、Jun-Hao Cui、Yu-Yu Dai、Xue-Mei Qiu、Wen-Hang Wang、Yue Zhou、Dan-Ping Chen、Cheng-Peng Li

  DOI：10.3390/molecules28083289

  日期：——

  A series of 1,4-naphthoquinone derivatives containing were synthesized as anti-cancer agents and the crystal structure of compound 5a was confirmed by X-ray diffraction. In addition, the inhibitory activities against four cancer cell lines (HepG2, A549, K562, and PC-3) were tested, respectively, and compound 5i showed significant cytotoxicity on the A549 cell line with the IC50 of 6.15 μM. Surprisingly, in the following preliminary biological experiments, we found that compound 5i induced autophagy by promoting the recycling of EGFR and signal transduction in the A549 cell, resulting in the activation of the EGFR signal pathway. The potential binding pattern between compound 5i and EGFR tyrosine kinase (PDB ID: 1M17) was also identified by molecular docking. Our research paves the way for further studies and the development of novel and powerful anti-cancer drugs.

  合成了一系列可用作抗癌剂的 1,4-萘醌衍生物，并通过 X 射线衍射证实了化合物 5a 的晶体结构。化合物 5i 对 A549 细胞株具有显著的细胞毒性，IC50 为 6.15 μM。令人惊讶的是，在接下来的初步生物学实验中，我们发现化合物 5i 通过促进表皮生长因子受体（EGFR）的循环和信号转导，诱导了 A549 细胞的自噬，从而激活了 EGFR 信号通路。分子对接还确定了化合物 5i 与表皮生长因子受体酪氨酸激酶（PDB ID：1M17）的潜在结合模式。我们的研究为进一步研究和开发新型强效抗癌药物铺平了道路。