- 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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- A facile greener synthesis, antimicrobial evaluation and molecular modelling of new 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-one derivatives
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Abstract: The synthesis of 4-aryl-2-(3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridin-2-yl)phthalazin-1(2H)-ones was performed by cyclization of 2-hydrazinyl-3-(2-(trifluoromethyl)phenyl)-1,8-naphthyridine with 2-aroylbenzoic acids in ethanol containing a catalytic amount of concentrated sulfuric acid under solid state conditions. All these synthesized compounds (8a–h) were screened for their in vitro antibacterial activity against gram-positive bacteria such as (Staphylococcus aureus) and gram-negative bacteria (Escherichia coli) and also evaluated for their antifungal activity against Aspergillus Niger and Helmenthosphorium oryzae fungal strains. Some of the products demonstrate good antibacterial activity and moderate antifungal activity. In predominantly, 8b, 8d, 8g, and 8h compounds showed good to excellent antibacterial and antifungal activities. The antimicrobial activity of the compound 8 was further investigated with the help of in LibDock score docking study to predict the active sites. Graphical abstract: [Figure not available: see fulltext.].
- Sakram, Boda,Ravi, Dharavath,Raghupathi, Mutyala,Kumar, Boda Sathish,Anantha Lakshmi
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p. 2007 - 2022
(2019/01/10)
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- The rotameric (R*,S*)- and (R*,R*)-biaryl-3,3′-diphthalides of polyphenylene series
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A wide range of diastereomeric pairs of biaryl-3,3′-diphthalides with aromatic (heteroaromatic) substituents of polyphenylene series (including halogen substituted) was synthesized. All of them were separated and characterized by the methods of X-ray analysis, HPLC, IR-, 1H and 13C NMR spectroscopy. It was determined that solubility, tendency to adsorption and related to it retention times, chemical shifts of equivalent hydrogen and carbon atoms of biaryl-3,3′-diphthalides diastereoisomers are determined firstly by the stereo-electronic effects of two adjacent strongly polar phthalide groups. It was shown that both in crystalline phase and in solution all the diphthalides, regardless of the chemical structure of their substituents, are existing as stable rotamers with cis or synperiplanar (chiral forms) and trans or antiperiplanar (meso-forms) conformation.
- Yangirov, Tagir A.,Fatykhov, Akhnef A.,Sedova, Elvira A.,Khalilov, Leonard M.,Meshcheryakova, Ekaterina S.,Ivanov, Sergey P.,Salazkin, Sergey N.,Kraikin, Vladimir A.
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p. 1282 - 1292
(2019/02/03)
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- Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti-Inflammatory and Anti-Proliferative Agents
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The chemistry of phthalazine derivatives has been of increasing interest since many of these compounds have found many chemotherapeutic applications. So this study aims to synthesize a library of phthalazine derivatives and to investigate their anti-inflammatory and anti-proliferative activities. Sixteen new phthalazinone derivatives (2a-p) were synthesized and tested for their in vitro antiproliferative and in vivo anti-inflammatory activities. All the synthesized compounds were identified and characterized by IR, 1H NMR, 13C NMR spectroscopy, and MS. Two compounds, 2b and 2i, showed significant anti-inflammatory activity comparable with that of the standard drug etoricoxib in the carrageenan-induced rat paw edema model at 3 and 5 h, respectively. Three compounds (2h, 2j, and 2g) showed moderate sensitivity toward the renal cancer cell line UO-31. A library of new phthalazone compounds (2a-p) was synthesized as dual inhibitors (COX-2/LOX-5) and evaluated for their anti-inflammatory, anticancer activities. Two compounds showed significant anti-inflammatory activity comparable with that of the standard drug etoricoxib, whereas three compounds showed moderate sensitivity toward the renal cancer cell line UO-31.
- Hameed, Alhamzah Dh.,Ovais, Syed,Yaseen, Raed,Rathore, Pooja,Samim, Mohammed,Singh, Surender,Sharma, Kalicharan,Akhtar, Mymona,Javed, Kalim
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p. 150 - 159
(2016/02/09)
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- LIQUID ARYLBENZOYL BENZOIC ACID ESTER DERIVATIVES FOR ENERGY CURABLE COMPOSITIONS
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4-Arylbenzoyl benzoic acid esters, such as the ethylhexyl esters and amyl esters of 4-phenylbenzoyl benzoic acid, are described, which are liquid and show excellent solubility in acrylic or methacrylic monomers. Compounds of Formula (1), wherein R1, R2, and A are as defined herein, are disclosed. They are suitable as components for radical photoinitiator systems for UV-curable compositions.
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Paragraph 0099; 0062
(2015/12/18)
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- Non-symmetric 9,10-diphenylanthracene-based deep-blue emitters with enhanced charge transport properties
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Realization of efficient deep-blue anthracene-based emitters with superior film-forming and charge transport properties is challenging. A series of non-symmetric 9,10-diphenylanthracenes (DPA) with phenyl and pentyl moieties at the 2nd position and alkyl groups at para positions of the 9,10-phenyls were synthesized and investigated. The non-symmetric substitution at the 2nd position enabled to improve film forming properties as compared to those of the unsubstituted DPA and resulted in glass transition temperatures of up to 92 °C. Small-sized and poorly conjugated substituents allowed to preserve emission in the deep blue range (-3-1 × 10 -2 cm2 V-1 s-1) in the solution-processed amorphous films of the DPA compounds.
- Serevicius, Tomas,Komskis, Regimantas,Adomenas, Povilas,Adomeniene, Ona,Jankauskas, Vygintas,Gruodis, Alytis,Kazlauskas, Karolis,Jursenas, Saulius
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p. 7089 - 7101
(2014/04/03)
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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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- Decarboxylative C-H arylation of benzoic acids under radical conditions
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A decarboxylative radical cyclization reaction has been developed for the synthesis of fluorenones. The reaction uses Ag(I)/K2S 2O8 to oxidatively decarboxylate an aroylbenzoic acid to an aryl radical, which undergoes cyclization to afford fluorenone products in good yield.
- Seo, Sangwon,Slater, Mark,Greaney, Michael F.
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supporting information; scheme or table
p. 2650 - 2653
(2012/07/27)
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- Fonctionnalisation d'hydrocarbures aromatiques polycycliques. Introduction de fonctions alcool, acide ou amine sur le biphenyle, le fluorene ou le phenanthrene
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With aluminium chloride as a catalyst, 3-methyl-1,3-butanediol, a primary-tertiary diol, yielded Friedel-Crafts primary alcohols with fluorene and biphenyl.The monosubstituted derivatives have been characterized mainly by 13C nmr and polysubstituted products have been obtained with excess diol.With the same substrates and in the same conditions a tertiary-tertiary diol such as 2,5-dimethyl-2,5-hexanediol gave only mono or bicycloalkylated hydrocarbons.The reactions of phtalic anhydride with fluorene, biphenyl and phenanthrene have been studied and the monosubstituted products characterized mainly by 13C nmr by means of a relaxation reagent.Bifunctionalized derivatives were also obtained and identified in the case of fluorene and biphenyl.On the other hand, amino functional groups were introduced on fluorene either by transformation of acid functions or by more direct routes such as reaction with isatoic anhydride or p-toluenesulfonylanthranilic acid.Some results have been used for the functionalization of an industrial residue containing polycyclic aromatic hydrocarbons.
- Guilhemat, Robert,Pereyre, Michel,Petraud, Michel
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p. 334 - 344
(2007/10/02)
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