- 2-(p-Toluoyl)benzoic acid
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The title compound, C15H12O3, crystallizes as a centrosymmetric dimer hydrogen bonded via the carboxylic acid groups. The carboxylic acid group is nearly coplanar with the adjacent aromatic ring, which is almost perpendicular to the tolyl ring. In contrast to all comparable o-benzoylbenzoic acid structures retrieved from the Cambridge Structural Database, the torsion angle between the carbonyl group linking both aromatic rings and the phenyl ring carrying the carboxylic acid group is less than 90°, resulting in a shorter distance between the two carbonyl O atoms.
- Degen, Alexander,Bolte, Michael
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Read Online
- Construction of an isoquinolinone framework from carboxylic-ester-directed umpolung ring opening of methylenecyclopropanes
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An interesting type of reaction involving functionalized methylenecyclopropanes (MCPs) has been revealed. Here, a nucleophilic attack of an anionic species onto a partially polarity-reversed MCP was realized by treating a neighbouring carboxylic ester tethered to the MCP and amine with KHMDS to realize an umpolung ring opening of the MCP. This work established an operationally convenient protocol for the rapid construction of isoquinolinone frameworks. This journal is
- Wei, Hao-Zhao,Wei, Yin,Shi, Min
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supporting information
p. 11201 - 11204
(2021/11/09)
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- (E)-2-Styrylanthracene-9,10-dione: A new type of fluorescent probe core and its application in specific mitochondria imaging
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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.
- Lu, Peng-fei,Meng, Fan-hao,Wang, Lin,Wang, Qiu-yin,Wang, Zhao-ran,Zhang, Ting-jian,Zhang, Xu,Zhao, Hai-yang
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- Friedel - gram acylating reaction method based on phthalic anhydride and aromatic alkyl compound
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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.
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Paragraph 0032-0042
(2021/09/08)
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- Tetracyano-anthraquinone dimethane micromolecular receptor material as well as preparation method and application thereof
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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.
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Paragraph 0059; 0063-0065; 0078; 0082-0084
(2020/05/11)
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- Mechanochemical Friedel-crafts acylations
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Friedel-Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.
- Dud, Mateja,Bri?, Anamarija,Ju?inski, Iva,Gracin, Davor,Margeti?, Davor
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supporting information
p. 1313 - 1320
(2019/07/08)
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- Metal-Free Arylation-Lactonization Sequence of γ-Alkenoic Acids Using Anilines as Aryl Radical Precursors
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The presence of salicylic acid (10 mol-%) and H2O (10 equiv.) significantly improves the arylation-lactonization sequence of γ-alkenoic acids with in situ formed diazonium salts (from bench stable anilines). The reaction is finished in less than 5 h without thermal or photochemical activation, giving access to a variety of γ,γ-disubstituted butyrolactones. The protocol is user-friendly and can be used at gram-scale or adapted to transform alkenols into phthalanes. Control experiments revealed that aryl radicals participate in the reaction and a plausible mechanism is proposed to include this and other mechanistic investigations, for the catalyzed and the background reaction.
- Felipe-Blanco, Diego,Gonzalez-Gomez, Jose C.
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supporting information
p. 7735 - 7744
(2019/12/24)
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- Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors
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A series of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives (1a–j) was designed and synthesized as novel xanthine oxidase inhibitors. Among them, the L/D-phenylalanine derivatives (1d and 1i) and the L/D-tryptophan derivatives (1e and 1j) were effective with micromolar level potency. In particular, the L-phenylalanine derivative 1d (IC50?=?3.0?μm) and the D-phenylalanine derivative 1i (IC50?=?2.9?μm) presented the highest potency and were both more potent than the positive control allopurinol (IC50?=?8.1?μm). Preliminary SAR analysis pointed that an aromatic amino acid fragment, for example, phenylalanine or tryptophan, was essential for the inhibition; the D-amino acid derivative presented equal or greater potency compared to its L-enantiomer; and the 9,10-anthraquinone moiety was welcome for the inhibition. Molecular simulations provided rational binding models for compounds 1d and 1i in the xanthine oxidase active pocket. As a result, compounds 1d and 1i could be promising lead compounds for further investigation.
- Zhang, Ting-Jian,Li, Song-Ye,Yuan, Wei-Yan,Zhang, Yi,Meng, Fan-Hao
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p. 893 - 901
(2018/03/21)
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- Discovery and biological evaluation of some (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety as potent xanthine oxidase inhibitors
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A series of (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety were synthesized and identified as novel xanthine oxidase inhibitors. Among them, the most promising compounds 1h and 1k were obtained with IC50values of 0.6?μM and 0.8?μM, respectively, which were more than 10-fold potent compared with allopurinol. The Lineweaver-Burk plot revealed that compound 1h acted as a mixed-type xanthine oxidase inhibitor. SAR analysis showed that the benzaldehyde moiety played a more important role than the anthraquinone moiety for inhibition potency. The basis of significant inhibition of xanthine oxidase by 1h was rationalized by molecular modeling studies.
- Zhang, Ting-jian,Li, Song-ye,Yuan, Wei-yan,Wu, Qing-xia,Wang, Lin,Yang, Su,Sun, Qi,Meng, Fan-hao
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supporting information
p. 729 - 732
(2017/02/18)
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- 2 - substituted - 9, 10 - anthraquinone compound, preparation method and use thereof
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The invention belongs to the technical field of medicine, and particularly relates to 2-substituted-9,10-anthraquinone compounds represented by the general formula I, the general formula II, the general formula III and the general formula IV, and pharmaceutically acceptable salts, hydrates or solvates and pharmaceutically acceptable carriers thereof. A preparation method comprises the steps: with phthalic anhydride as a starting material, carrying out a Friedel-Crafts reaction, concentrated sulfuric acid dehydration, NBS bromization and sodium azide substitution, generating a key intermediate 2-azide methyl-9,10-anthraquinone, and finally in the presence of copper sulfate pentahydrate and vitamin C, carrying out a Husigen cycloaddition reaction with substituted alkyne; or carrying out concentrated sulfuric acid dehydration, cyclization, chromium trioxide oxidation and thionyl chloride chlorination, to obtain anthraquinone-2-formyl chloride, then carrying out an acylation reaction with various L-amino acid methyl esters, further hydrolyzing, and thus obtaining the target compounds. The prepared compounds show good results in in-vitro antitumor activity tests.
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Paragraph 0088-0091
(2017/08/15)
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- arone and amide compound and its preparation and use in medicine
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The invention discloses a novel arone and arylamide compound represented by formula I, a cistrans isomer, physiologically acceptable salts, a solvate and a crystallizing form thereof, a preparation method of the compound, a medicine preparation containing the compound and clinical application of the compound in treating diseases related to protein tyrosine phosphatases 1B.
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Paragraph 0112; 0114; 0115
(2017/11/17)
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- Ultrasound-promoted Friedel-Crafts acylation of arenes and cyclic anhydrides catalyzed by ionic liquid of [bmim]Br/AlCl3
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A simple and efficient method of Friedel-Crafts acylation of arenes with succinic anhydride, phthalic anhydride and glutaric anhydride under the action of 1-butyl-3-ethylimidazolium ([bmim]Br/AlCl3 ([bmim]+) cation (ionic liquid) and ultrasound irradiation is presented. Thy purity of products was tested by GC-MS and their structures evaluated by IR and 1H NMR spectroscopy.
- Fekri, Leila Zare,Nikpassand, Mohammad
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p. 1825 - 1829
(2015/01/09)
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- Synthesis and blood glucose lowering activity of some novel benzenesulfonylthiourea derivatives substituted with 4-aryl-1-oxophthalazin- 2(1H)yl-ones
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Some new benzenesulfonylthiourea derivatives substituted with phthalazones (2a-q) were synthesized by refluxing the appropriate 4-aryl-1-oxophthalazin- 2(1H)yl benzenesulfonamides with isothiocyanate in dry acetone over anhydrous K2CO3. All the synthesized compounds were characterized on the basis of IR, 1H NMR, MS data and elemental analysis. These synthesized compounds (2a-q) at the dose of 20 mg/kg were tested for antihyperglycemic activity in the glucose-fed hyperglycemic normal rat model and among these compounds 2f and 2m showed modest antihyperglycemic activity.
- Yaseen, Shafiya,Bashir, Rafia,Ovais, Syed,Rathore, Pooja,Samim, Mohammed,Javed, Kalim
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p. 362 - 366
(2014/06/09)
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- Synthesis and biological evaluation of 4-arylphthalazones bearing benzenesulfonamide as anti-inflammatory and anti-cancer agents
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Nine 4-arylphthalazones bearing benzenesulfonamide (2a-i) were synthesized by the condensation of the appropriate 2-aroylbenzoic acid (1a-i) and 4-hydrazinobenzenesulfonamide in ethanol. The structures of these compounds were elucidated by elemental analysis, IR, 1H NMR, 13C NMR, and MS spectroscopy. Two compounds, 2b and 2i, showed significant anti-inflammatory activity comparable to that of the standard drug celecoxib in the carrageenan-induced rat paw edema model. These compounds (2b and 2i) had selective inhibitory activity towards the COX-2 enzyme. Compound 2b had a better selectivity ratio (COX-1/COX-2) compared to that of celecoxib and can be used as a novel template for the design of selective COX-2 inhibitors. Compounds 2d and 2i were screened for their antiproliferative activity toward 60 human cancer cell lines by the National Cancer Institute (USA). The compounds 2d and 2i displayed mild activity toward the renal cancer cell line UO-31. Nine 4-arylphthalazones bearing benzenesulfonamide (2a-i) were synthesized by the condensation of the appropriate 2-aroylbenzoic acid (1a-i) and 4-hydrazinobenzenesulfonamide in ethanol. Compounds 2b and 2i showed anti-inflammatory activity comparable to that of celecoxib in the carrageenan-induced rat paw edema model. Compounds 2d and 2i were screened for their antiproliferative activity towards 60 human cancer cell lines, displaying mild activity toward the renal cancer cell line UO-31. Copyright
- Yaseen, Shafiya,Ovais, Syed,Bashir, Rafia,Rathore, Pooja,Samim, Mohammed,Singh, Surender,Nair, Vinod,Javed, Kalim
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p. 491 - 498
(2013/07/26)
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- Palladium-catalyzed chemoselective decarboxylative ortho acylation of benzoic acids with α-oxocarboxylic acids
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Palladium-catalyzed chemoselective decarboxylative cross coupling of benzoic acids with α-oxocarboxylic acids was realized via an arene sp 2 C-H functionalization process. This work represents the first example of transition-metal-catalyzed cro
- Miao, Jinmin,Ge, Haibo
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supporting information
p. 2930 - 2933
(2013/07/26)
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- 2-Hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylic Acid with Inbuilt β-NHydroxy-γ-keto-Acid pharmacophore as HCV NS5B polymerase inhibitors
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The inbuilt 2-N-hydroxy-1-oxo-3-carboxylic acid of isoquinolone was designed as pyrophosphate mimic for hepatitis C NS5B polymerase. Various 2-hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid derivatives 11a-p were synthesized and evaluated as HCV NS5B polymerase inhibitors. Compound 11c exhibited moderate inhibitory potency based on the inorganic pyrophosphate generation (IC50 = 9.5 μM) and based on NTP incorporation by NS5B enzyme (IC50 = 5.9 μM). Compound 11c demonstrated antiviral activity (EC50 = 15.7 μM) and good selectivity in HCV genotype 1b replicon Ava.5 cells. Compound 11c reduced the interaction of NTP to NS5B polymerase. Docking model showed that 11c situated in similar orientation to the bound uridine triphosphate in the active site of NS5B polymerase. As a result, 2-hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid was disclosed as a novel inbuilt β-Nhydroxy-γ-keto-acid pharmacophore for HCV NS5B polymerase inhibitors.
- Deore,Chen,Chen,Chang,Chuang,Chern,Wang,Chern
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body text
p. 613 - 624
(2012/07/28)
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- A rapid and efficient access to diaryldibenzo[b,f][1,5]diazocines
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2-Benzoylbenzoyl azides undergo facile cyclization under acidic conditions to give substituted dibenzo[b,f][1,5]-diazocines in good yields. This approach shortens the synthetic steps toward these compounds as compared with conventional methods. The mechanism of the diazocine synthesis is assumed to proceed by an unprecedented intermolecular [2 + 2] cyclization.
- Wang, Xiao,Li, Jianzhong,Zhao, Na,Wan, Xiaobo
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supporting information; experimental part
p. 709 - 711
(2011/04/24)
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- An efficient one-pot synthesis of pyridazinones and phthalazinones using HY-zeolite
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Figure represented. The first one-pot synthesis of pyridazinones and phthalazinones from arenes, cyclic anhydrides, and ArNHNH2 in the presence of efficient recyclable heterogeneous catalyst, HY-zeolite, in high yield and short reaction time is reported.
- Zare, Leila,Mahmoodi, Nosratollah,Yahyazadeh, Asieh,Mamaghani, Manouchehr,Tabatabaeian, Khalil
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experimental part
p. 864 - 867
(2011/09/16)
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- Synthesis, crystal structure and biological activities of four novel tetranuclear di-organotin(IV) carboxylates
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Four complexes: [Bu2(L1)SnOSn(L1)Bu2]2 (1), [Bu2(L2)SnOSn(L2)Bu2]2 (2), [Bu2(L3)SnOSn(L3)Bu2]2 (3), and [Bu2(L4)SnOSn(L4)Bu2]2 (4), (HL1 = 2-(4-methylbenzoyl)benzoic acid, HL2 = 2-(2,4-diethylbenzoyl)benzoic acid, HL3 = 2-(4-chlorobenzoyl)benzoic acid, HL4 = 2-(4-isopropylbenzoyl)benzoic acid) have been prepared and structurally characterized by means of elemental analysis and vibrational, 1H NMR and FT-IR spectroscopies. The crystal structures of all complexes have been determined by X-ray crystallography. Three distannoxane rings are present to the dimeric tetraorganodistannoxane of planar ladder arrangement. Each structure is centro-symmetric and features a central rhombus Sn2O2 unit with two additional tin atoms linked at the O atoms. Complex 1 exhibited good antibacterial and antitumor activities and have a potential to be used as drugs.
- Kang, Wanli,Wu, Xiaoyan,Huang, Jianbin
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experimental part
p. 2402 - 2408
(2009/09/30)
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- Nonsteroidal anti-inflammatory drugs and their analogues as inhibitors of aldo-keto reductase AKR1C3: New lead compounds for the development of anticancer agents
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Nonsteroidal anti-inflammatory drugs (NSAIDs) like indomethacin, flufenamic acid, and related compounds have been recently identified as potent inhibitors of AKR1C3. We report that some other NSAIDs (diclofenac and naproxen) also inhibit AKR1C3, with the IC50 values in the low micromolar range. In order to obtain more information about the structure-activity relationship and to identify new leads, a series of compounds designed on the basis of NSAIDs were synthesized and screened on AKR1C3. The most active compounds were 2-[(2,2-diphenylacetyl)amino]benzoic acid 4 (IC50 = 11 μM) and 3-phenoxybenzoic acid 10 (IC50 = 0.68 μM). These compounds represent promising starting points for the development of new anticancer agents.
- Gobec, Stanislav,Brozic, Petra,Rizner, Tea Lanisnik
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p. 5170 - 5175
(2007/10/03)
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- Direct Synthesis of γ-Substituted Phthalides Via ortho-Aryl Benzoic Acid Mediated Benzyl Radical Cyclization
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Direct synthesis of γ-substituted phthalids from related ortho-aryl benzoic acids with 48-85% yield are covered. The direct oxidation in the presence of peroxydisulphate-copper (II) chloride in aqueous medium was applied. The reaction is highly regioselective and leads exclusively to γ-butyrolactone, through very stable benzylic radical intermediate.
- Mahmoodi,Salehpour
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p. 875 - 878
(2007/10/03)
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- An alternative route to syntheses of aryl keto acids in a chloroaluminate ionic liquid
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The Lewis acidic 1-butyl-3-methylimidazolium chloroaluminate ionic liquid [bmim]Cl.AlCl3, N=0.67, is employed as a catalyst as well as the solvent for the quick and efficient syntheses of aryl keto acids by Friedel-Crafts acylation and aroylation of aromatic hydrocarbons using cyclic acid anhydrides.
- Mohile, Swapnil S.,Potdar, Mahesh K.,Salunkhe, Manikrao M.
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p. 650 - 651
(2007/10/03)
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- Direct synthesis of γ-substituted phthalides by cyclization of benzyl radicals generated from o-(arylmethyl)benzoic acids
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Direct oxidation of o-(arylmethyl)benzoic acids with sodium peroxysulfate-copper(II) chloride in water yields γ-substituted phthalides. The reaction is highly regioselective, and the corresponding γ-butyro-lactones are the only products formed through intermediate stable arylmethyl radicals.
- Mahmoodi,Salehpour
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p. 1760 - 1763
(2007/10/03)
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- Friedel-crafts alkylation and acylation in the absence of solvent
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A short and efficient synthetic route, for alkylation and acylation of aromatic compounds in the absence of solvent is developed. According to the reaction system and conditions used, different alkyl-, and acyl arenes are obtained in moderate to good yields. The structures are assigned by 1H and 13C NMR spectroscopy.
- Ghiaci,Asghari
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p. 2213 - 2220
(2007/10/03)
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- AlCl3-DMF Complex as Catalyst in the Fredel-Crafts Reaction. The Reactivity of Anhydrides and Chlorides of Dicarboxylic Acids.
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This paper reports different examples of Friedel-Crafts acylation of various substrates with dicarboxylic acid chlorides (phthalic, isophthalic, and malonyl synthons) in the presence of the AlCl3-DMF complex as catalyst.When we reacted 2(3H)-benzothiazolone with phthalic anhydride in the presence of the AlCl3-DMF complex as catalyst in addition to the product of 6-substitution, 4-(2-carboxybenzoyl) 2(3H)-benzothiazolone was obtained as a contaminant.This is the first product ever obtained with a 4-substitution in the acylation of 2(3H)-benzothiazolone.
- Taverne, Thierry,Depreux, Patrick,Lasieur, Daniel,Henichart, Jean-Pierre,Poupaert, Jacques H.
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p. 791 - 802
(2007/10/03)
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- The reaction of arylcoppermagnesium and other organometallic reagents with phthalic anhydride
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Arylcoppermagnesium reagents, prepared from 5ArMgX + 2.5CuI, (Ar = 4-CH3C6H4, 4-CH3OC6H4, 4-ClC6H4, 2-C4H3S) react with one equivalent of phthalic anhydride in ether or THF at -5 deg C for 2.5 h to give 2-aroylbenzoic acid in 83-98percent yields.The phenylcoppermagnesium reagent (Ar = C6H5) under similar conditions gives 2-benzoylbenzoic acid and 3,3-diphenylphthalide in 40-42percent and 42-45percent yield, respectively.The yield of the 2-benzoylbenzoic acid rises to 93percent in the presence of dimethyl sulphide.Under these conditions no phthalide is formed.Lithium diphenylcuprate reactswith phthalic anhydride in ether-hexane to give 92percent of 2-benzoylbenzoic acid and 7percent of 3,3-diphenylphthalide.The reaction of phenylcopper reagent, prepared from PhMgBr + CuI, under similar conditions is slow and gives 2-benzoylbenzoic acid in 15percent yield.The reaction of phenylmagnesium bromide in the presence or absence of catalytic amounts of copper(I) iodide gives unsatisfactory results.Use of two equivalents of phenyllithium with one equivalent of phthalic anhydride, on the other hand, affords 3,3-diphenylphthalide in 77percent yield.The mechanisms of these reactions are discussed.
- Rahman, Mohammed T.,Nahar, Syeda K.
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p. 201 - 208
(2007/10/02)
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- THE SYNTHESIS OF SOME MONOMETHYLANTHRACENAMINES
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The synthesis of 2-methyl-1-anthracenamine (2), 3-methyl-1-anthracenamine (7), 4-methyl-1-anthracenamine (14), 1-methyl-2-anthracenamine (20), 3-methyl-2-anthracenamine (26), and 1-methyl-3-anthracenamine (3) from the corresponding 9,10-anthraquinones in order to confirm their presence in coal-derived products is reported.
- Castle, Raymond N.,Kudo, Hirotaka,Lee, Milton L.
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p. 2269 - 2277
(2007/10/02)
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- Aluminum catalysts
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An aluminum halide complex of an aluminum halide, a hydrogen halide and an alkylbenzene is prepared by continuously feeding a gaseous hydrogen halide to a reaction zone comprising aluminum and an alkylbenzene and continuously taking the resulting aluminum halide complex out of the reaction zone, the byproduced hydrogen gas being taken out of the reaction zone, and aluminum and the alkylbenzene being fed continuously or intermittently to the reaction zone.
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