84-54-8Relevant articles and documents
Photoinduced electron transfer between 2-methylanthraquinone and triethylamine in an ionic liquid: Time-resolved EPR and transient absorption spectroscopy study
Zhu, Guanglai,Wang, Yu,Fu, Haiying,Xu, Xinsheng,Cui, Zhifeng,Ji, Xuehan,Wu, Guozhong
, p. 148 - 153 (2015)
Photoinduced electron transfer between 2-methylanthraquinone (MeAQ) and triethylamine (TEA) in a room-temperature ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]), was investigated by comparing the time-resolved electron paramagnetic resonance (TR-EPR) spectroscopy and the transient absorption spectroscopy. The results of TR-EPR spectroscopy, in which MeAQ was 8 mmol L-1and TEA was 150 mmol L-1, indicated that the transient radical would exist longer time in [bmim][PF6] than in acetonitrile. At the delay time of 8 μs after laser excitation, the TR-EPR signal transformed from an emissive peak into an absorptive peak when the experiment was performed in [bmim][PF6]. The results of the transient absorption spectroscopy, in which MeAQ was 0.1 mmol L-1and TEA was 2.2 mmol L-1, showed that the efficiency and the rate of the photoinduced electron transfer reaction in [bmim][PF6] were obviously lower than that in acetonitrile. It was concluded that various factors, such as concentration, viscosity and local structural transformation of the solution, have an influence on the process of photoinduced electron transfer in [bmim][PF6].
Liquid-phase cascade acylation/dehydration over various zeolite catalysts to synthesize 2-methylanthraquinone through an efficient one-pot strategy
Hou, Qijun,Zheng, Bumei,Bi, Chenguang,Luan, Jimei,Zhao, Zhongkui,Guo, Hongchen,Wang, Guiru,Li, Zongshi
, p. 376 - 383 (2009)
Liquid-phase cascade acylation/dehydration reactions over various zeolite catalysts were performed to synthesize 2-methylanthraquinone (2-MAQ). Many characterization techniques such as NH3-TPD, pyridine- IR, BET, XRD, SEM, TEM, XRF, and TGA have been employed to study the relationship between the catalytic behavior and the nature of catalysts. The present work provides evidence that the acidity, pore size, particle size, and surface area of zeolites strongly affect both the catalytic properties and the coke formation. Moreover, it is discovered that the reaction activity of phthalic acid (PA) is higher than that of phthalic anhydride, and the yield of 2-MAQ reached 82.2% when PA was used, which opened a new avenue for one-pot synthesizing 2-MAQ by using PA as an acylation reagent. The catalyst can be recycled four times only with a slight decrease in activity. The nano-sized H-beta zeolite could be a promising liquid-phase cascade acylation/dehydration catalyst for clean one-pot synthesis of 2-MAQ.
Electroreductive Cleavage of Substituted 9,10-Anthraquinones in 50percent Aqueous THF Buffers: A pH-Dependent Process
Blankespoor, Ronald L.,Hsung, Richard,Schutt, David L.
, p. 3032 - 3035 (1988)
A variety of substituted 9,10-anthraquinones with acetate leaving groups (4a-7a) were reduced at a glassy carbon electrode in 50percent aqueous THF prepared from aqueous buffers at pH 6, 7, and 8.Cyclic voltammograms of these compounds exhibited a single reduction wave with Ep values of -450 to -530 mV (vs Ag/AgCl/0.10 M Cl-) at pH 7.Ep shifted to more negative values with increasing pH (45-50 mV/pH unit) consistent with a 2e-/2H+ reduction process which converts 4a-7a to their corresponding anthrahydroquinones.Constant potential reduction of acetates 4a-7a at -800 mV at pH 6 or 7 gave n values of 2.2-2.4.Air oxidation of the catholytes, a procedure that converts anthrahydroquinones to anthraquinones, led to a 56-89percent recovery of the acetates and 7-32percent yields of the reductive cleavage products 4b-7b.In contrast, electroreduction of 4a-7a at pH 8 gave much higher yields (50-73percent) of 4b-7b with n values of 3.5-3.8.This pH-dependent process suggests that 4a-7a cleave much slower via their intermediate anthrahydroquinones than the conjugate bases of their anthrahydroquinones, which are present in relatively high concentration at higher pH.NaOH titration curves of the anthrahydroquinones of 5a and 5b support this mechanistic picture.
(E)-2-Styrylanthracene-9,10-dione: A new type of fluorescent probe core and its application in specific mitochondria imaging
Lu, Peng-fei,Meng, Fan-hao,Wang, Lin,Wang, Qiu-yin,Wang, Zhao-ran,Zhang, Ting-jian,Zhang, Xu,Zhao, Hai-yang
, (2021/09/20)
Herein, a new type of fluorescent probe core, (E)-2-styrylanthracene-9,10-dione (EK01), was developed which displayed strong fluorescence quantum yield (Φ = 0.867 in DMF; Φ = 0.561 in acetone; Φ = 0.616 in CH2Cl2; Φ = 0.265 in DMSO), good photostability, large stokes shift (90 nm–120 nm) and molar extinction coefficients (0.5875 × 104–0.7609 × 104 mol?1 L cm?1). During cell assays and co-localization experiments, EK01 showed excellent cell membrane permeability and low cytotoxicity against MCF-10A (human mammary epithelial cell line) and HT-29 (human colorectal adenocarcinoma cell line). Particularly, we surprisingly discovered that EK01 could selectively aggregate in mitochondria and specific stain it in a green emissive fluorescent form, which means that EK01 could be a real-time specifically monitor of mitochondria in living cells with a high signal-to-noise ratio. Hence a new mitochondria imaging method was established which is incubating EK01 with living cells for 1 h at a final concentration of 6–12 μM, then visualizing under a confocal microscope at 395 nm. It is worth noting that the fluorescence efficiency of EK01 is not outstanding in organisms, it has much stronger fluorescence efficiency in other organic solvent systems (such as DMF, acetone and CH2Cl2). Therefore, as a new type of fluorescent core that is easy to synthesis and graft, we believe that (E)-2-styrylanthracene-9,10-diones have the potential to develop a variety of fluorescence platforms applying in different fields.
Friedel - gram acylating reaction method based on phthalic anhydride and aromatic alkyl compound
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Paragraph 0043-0045, (2021/09/08)
A part of a substituted alkylbenzene is used as a solvent and a reaction raw material for - gram acylating reaction, a part of a substituted alkylbenzene is dissolved in a reaction raw material phthalic anhydride and a chloroaluminate ionic liquid catalyst, and a residual part of a substituted alkylbenzene is added dropwise - to obtain - (2 - 4' - alkylbenzoyl) benzoic acid intermediate. 2 -position positioning selectivity of the method is higher, and the reaction production cost is low.
Inhibitory activities of anthraquinone and xanthone derivatives against transthyretin amyloidogenesis
Kitakami, Ryota,Inui, Kishin,Nakagawa, Yusuke,Sawai, Yurika,Katayama, Wakana,Yokoyama, Takeshi,Okada, Takuya,Kanamitsu, Kayoko,Nakagawa, Shinsaku,Toyooka, Naoki,Mizuguchi, Mineyuki
, (2021/07/06)
Transthyretin is a tetrameric protein which functions as a transporter of thyroxine and retinol-binding protein. Misfolding and amyloid aggregation of transthyretin are known to cause wild-type and hereditary transthyretin amyloidosis. Stabilization of the transthyretin tetramer by low molecular weight compounds is an efficacious strategy to inhibit the aggregation pathway in the amyloidosis. Here, we investigated the inhibitory activities of anthraquinone and xanthone derivatives against amyloid aggregation, and found that xanthone-2-carboxylic acid with one chlorine or methyl group has strong inhibitory activity comparable with that of diflunisal, which is one of the best known stabilizers of transthyretin. X-ray crystallographic structures of transthyretin in complex with the compounds revealed that the introduction of chlorine, which is buried in a hydrophobic region, is important for the strong inhibitory effect of the stabilizer against amyloidogenesis. An in vitro absorption, distribution, metabolism and elimination (ADME) study and in vivo pharmacokinetic study demonstrated that the compounds have drug-like features, suggesting that they have potential as therapeutic agents to stabilize transthyretin.
Tetracyano-anthraquinone dimethane micromolecular receptor material as well as preparation method and application thereof
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Paragraph 0059; 0066-0068; 0078; 0085-0087, (2020/05/11)
The invention relates to a tetracyano-anthraquinone dimethane micromolecular acceptor material as well as a preparation method and application thereof. The structure of the acceptor material is as shown in a formula I, which is described in the specification. The micromolecular acceptor material has good solubility and stability, the absorption spectrum is well matched with the solar spectrum, andthe micromolecular acceptor material can be used for organic solar cells.
Cathodic electroorganic reaction on silicon oxide dielectric electrode
Shin, Samuel J.,Park, Sangmee,Lee, Jin-Young,Lee, Jae Gyeong,Yun, Jeongse,Hwang, Dae-Woong,Chung, Taek Dong
, p. 32939 - 32946 (2021/02/05)
The faradaic reaction at the insulator is counterintuitive. For this reason, electroorganic reactions at the dielectric layer have been scarcely investigated despite their interesting aspects and opportunities. In particular, the cathodic reaction at a silicon oxide surface under a negative potential bias remains unexplored. In this study, we utilize defective 200-nm-thick n+-Si/SiO2 as a dielectric electrode for electrolysis in an H-type divided cell to demonstrate the cathodic electroorganic reaction of anthracene and its derivatives. Intriguingly, the oxidized products are generated at the cathode. The experiments under various conditions provide consistent evidence supporting that the electrochemically generated hydrogen species, supposedly the hydrogen atom, is responsible for this phenomenon. The electrogenerated hydrogen species at the dielectric layer suggests a synthetic strategy for organic molecules.
Green synthesis method for preparing 2-alkylanthraquinone from phthalic anhydride in one step
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Paragraph 0034-0035; 0042-0045, (2020/06/16)
The invention relates to the technical field of green synthesis of organic matters. The invention relates to a synthetic method, in particular to a green synthetic method for preparing 2-alkylanthraquinone from phthalic anhydride in one step. According to the method, phthalic anhydride and alkylbenzene are used as raw materials, difunctional sulfonic acid type solid acid based on an HZSM-5 molecular sieve is used as a catalyst, phthalic anhydride and alkylbenzene are catalyzed to be subjected to a Friedel-Crafts acylation reaction and a dehydration cyclization reaction at the same time under the action of the catalyst, so that the 2-alkyl anthraquinone is prepared in one step, wherein the bifunctional sulfonic acid type solid acid based on the HZSM-5 molecular sieve is a sulfonic acid typeHZSM-5 molecular sieve obtained by carrying out sulfonation treatment on the HZSM-5 molecular sieve. According to the synthesis method of the 2-alkyl anthraquinone, the bifunctional (with strong Bronsted acidity and Lewis acidity) sulfonic acid type solid acid based on the HZSM-5 molecular sieve is used as the catalyst to replace AlCl3 and fuming sulfuric acid, so that generation of a large amount of waste residues, waste gas and wastewater is avoided, and green production is realized.
Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances
Li, Yuying,Guo, Fang,Chen, Tinggui,Zhang, Liwei,Wang, Zhuanhua,Su, Qiang,Feng, Liheng
, (2020/09/04)
The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.
