- 1,4-Naphthoquinones potently inhibiting P2X7 receptor activity
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P2X7 receptor (P2X7R) is an ATP-gated ion-channel with potential therapeutic applications. In this study, we prepared and searched a series of 1,4-naphthoquinones derivatives to evaluate their antagonistic effect on both human and murine P2X7 receptors. W
- Faria,Oliveira,Salles,Oliveira,von Ranke,Bello,Rodrigues,Castro,Louvis,Martins,Ferreira
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- Suzuki-Miyaura coupling between 3-iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities
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A series of 2-hydroxy-3-arylnaphthalene-1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N,N-diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.
- Gomes, Sara L. S.,Milit?o, Gardenia C. G.,Costa, Arinice M.,Pessoa, Cláudia ó.,Costa-Lotufo, Letícia V.,Cunha, Edézio F.,Torres-Santos, Eduardo C.,Costa, Paulo R. R.,Da Silva, Alcides J. M.
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- Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction
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An unprecedented Pd(II)-catalyzed decarbonylative C-H/C-C activation and annulation reaction, which proceeds via intramolecular cyclization, is reported. This reaction of hydroxynaphthoquinones with disubstituted alkynes provides good yields of substituted alkylidene phthalides, which are the key intermediates for the synthesis of bioactive natural products.
- Borthakur, Somadrita,Baruah, Swagata,Sarma, Bipul,Gogoi, Sanjib
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p. 2768 - 2771
(2019/04/16)
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- Pd/C-catalyzed dehydrogenation of 2-cinnamoylbenzoic acids to 3-benzylidene-3H-isochroman-1,4-diones
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Pd/C, a widely accepted hydrogenation catalyst, is found to catalytically dehydrogenate 2-cinnamoylbenzoic acids to 3-benzylidene-3-H-isochroman-1,4-diones with H2 as the only byproduct. This synthetic reaction proceeds without oxidants and hydrogen acceptors, thereby representing an atom- and step-efficient approach to a wide range of functionalized 3-benzylidene-3H-isochroman-1,4-diones.
- Yang, Dejun,Ji, Xuan,Zhang, Jie,Zhang, Chenyang,Li, Mingfei,Li, Jin,Liu, Renhua
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supporting information
p. 7774 - 7777
(2018/07/25)
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- Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione
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Selective C vs N-arylation of 2-aminonaphthoquinone was achieved using different transition metal salts and arylboronic acids. Mn(OAc)3·2H2O provided C-arylated product whereas NiCl2·6H2O and Cu(OAc)2
- Ashok, Polu,Ilangovan, Andivelu
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supporting information
p. 438 - 441
(2018/01/03)
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- Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones-green palladium-catalysed Suzuki cross coupling
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Quinones are important scaffolds that are present in a variety of natural products or synthetic bioactive molecules. Arylation is an important strategy for accomplishing structural modifications, leading to new potential candidates for use as drugs. In the present work, palladium-catalysed, ligandless and phosphine-free Suzuki coupling reactions between 2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated. The Osiris and Molinspiration Cheminformatics programs, utilizing in silico analyses, imply that these naphthoquinones are candidates for use as drugs which was reinforced by the outcomes of the in vitro antifungal and trypanocidal activity tests. Our in vitro data indicated a MIC value of 8 μg mL-1 against Candida albicans ATCC 24433 strains, and an EC50 of 0.67 μM with respect to trypanocidal activity against Trypanosoma cruzi epimastigote strains (Y).
- Louvis, Aline Da R.,Silva, Nayane A. A.,Semaan, Felipe S.,Da Silva, Fernando De C.,Saramago, Gabriela,De Souza, Laís C. S. V.,Ferreira, Bruno L. A.,Castro, Helena C.,Salles, Juliana P.,Souza, André L. A.,Faria, Robson X.,Ferreira, Vitor F.,Martins, Daniela De L.
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p. 7643 - 7656
(2016/09/28)
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- Aryl-free radical-mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application toward the synthesis of benzocarbazoledione
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Oxidative arylation of naphthoquinones has been developed through combination of o-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor-antibiotic precursor such as benzocarbazoledione.
- Patil, Pravin,Nimonkar, Abhay,Akamanchi, Krishnacharya G.
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p. 2331 - 2336
(2014/04/03)
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- Discovery and development of an efficient process to atovaquone
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The discovery and development of an efficient and more sustainable manufacturing route to the antipneumocystic agent atovaquone (2-((1R,4R)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione) 1 is described. The existing commercial route to atovaquone delivers a poor yield of product and uses expensive reagents. The new synthesis commences with readily available phthalic anhydride, which is converted to 1,4-isochromandione 5 and then to atovaquone 1 by reaction with 4-(4-chlorophenyl)cyclohexanecarboxylic acid 3 using key bromination, Rosenmund reduction, and rearrangement chemistries. Downstream processing to atovaquone is both high yielding and robust, and the resulting process has been demonstrated on 200-kg scale. The process is simple, uses cheap raw materials, and is more sustainable in that it avoids lowyielding silver-promoted chemistry and isomerisation procedures. It includes a robust, facile, and highly efficient procedure to 1,4-isochromandione 5, and routes to 4-(4-chlorophenyl)cyclohexanecarboxaldehyde 9 have also been developed, including a Rosenmund method that was demonstrated on pilot-plant scale. Also discussed are the route-derived impurities and processing amendments to control their formation.
- Britton, Hugh,Catterick, David,Dwyer, Andrew N.,Gordon, Andrew H.,Leach, Stuart G.,McCormick, Chris,Mountain, Clive E.,Simpson, Alec,Stevens, David R.,Urquhart, Michael W. J.,Wade, Charles E.,Warren, John,Wooster, Nick F.,Zilliox, Audrey
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p. 1607 - 1617
(2013/02/23)
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- Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes
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Phenyliodonium ylide of lawsone, activated by BF3·Et 2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1,4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3·Et2O- activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction.
- Glinis, Elias,Malamidou-Xenikaki, Elizabeth,Skouros, Haris,Spyroudis, Spyros,Tsanakopoulou, Maria
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experimental part
p. 5786 - 5792
(2010/09/09)
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- Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation
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A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.
- Allan, Kevin M.,Hong, Boram D.,Stoltz, Brian M.
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supporting information; experimental part
p. 4960 - 4964
(2010/02/15)
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- Functionalized hydroxyquinones through Suzuki-type coupling of phenyliodonium ylides of hydroxyquinones with arylboronic acids
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The palladium(II) acetate catalyzed reaction of phenyliodonium ylides of 2-hydroxyquinones with arylboronic acids affords a variety of 3-substituted 2-hydroxyquinone derivatives. Best yields are obtained by using tri(tert-butyl)phosphine as a ligand. Georg Thieme Verlag Stuttgart.
- Kazantzi, Georgia,Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros
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p. 2597 - 2600
(2008/09/16)
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- Studies on the chemistry of 2-(2-oxo-3-phenylpropyl)-benzaldehydes: Novel total synthesis of 3-phenylnaphthalen-2-ols and 2-hydroxy-3-phenyl-1,4- naphthoquinones
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We describe the first studies on the chemistry of 2-(2-oxo-3-phenylpropyl) benzaldehydes, which were converted into 3-benzylisochromen-1-ones via the corresponding 2-(2-oxo-3-phenylpropyl)benzoic acid. The 2-(2-oxo-3-phenylpropyl) benzaldehydes proved to be convenient starting materials for the synthesis of 3-phenyl-2-naphthols. Oxidation of the latter compounds resulted in a novel, efficient synthesis of 3-phenyl-1,2-naphthoquinones, which were efficiently transformed into 2-hydroxy-3-phenyl-1,4-naphthoquinones.
- Martínez, Ana,Fernández, Marcos,Estévez, Juan C.,Estévez, Ramón J.,Castedo, Luis
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p. 485 - 492
(2007/10/03)
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- Palladium-catalyzed synthesis of o-acetylbenzoic acids: A new, efficient general route to 2-hydroxy-3-phenyl-1,4-naphthoquinones and indolo[2,3-b]naphthalene-6,11-diones
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We describe here a new, efficient general synthesis of o-acetylbenzoic acids by Heck palladium-catalyzed arylation of n-butyl vinyl ether with o-bromobenzoic acid esters and the use of these compounds as starting materials for the synthesis of 3-benzylideneisochroman-1,4-diones, which readily rearrange to 2-hydroxy-3-phenyl-1,4-naphthoquinones. The application of this strategy to the synthesis of indolo[2,3-b]naphthalene-6,11-diones is also described.
- Barcia, José C,Cruces, Jacobo,Estévez, Juan C,Estévez, Ramón J,Castedo, Luis
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p. 5141 - 5144
(2007/10/03)
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- Selective phenylation of naphthoquinones and coumarins using diphenylmercury
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Under the influence of UV light, 1,4-naphthoquinones 1-5 and coumarins 6-10 on reaction with diphenylmercury in acetonitrile under nitrogen atmosphere give corresponding 2-phenyl-1,4-naphthoquinones 11-15 and 4-phenylcoumarins 16-20.
- Thaplial, Prakash Chander
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p. 477 - 479
(2007/10/03)
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- Regiospecific synthesis of unsymmetrical 2,3-Diarylquinones via stepwise Pd(O)-Catalyzed couplings of arylstannanes to doubly activated quinone equivalents
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Coupling of arylstannanes to 2-phenyliodonio-1,4-naphthoquinone-3-oxide in the presence of a tetrakis(triphenylphosphine)palladium(O)-cuprous iodide catalyst yields 3-aryl-2-hydroxy-1,4-naphthoquinones which are converted to the corresponding 3-aryl-2-trifluoromethanesulfonyloxy-1,4-naphthoquinone and coupled to a different arylstannane to yield unsymmetrical 2,3-diaryl-1,4-naphthoquinones in good yields.
- Stagliano, Kenneth W.,Malinakova, Helena C.
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p. 6617 - 6620
(2007/10/03)
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- Spiro Epoxy Ketones. 2. Thermal Transformations of 2-Benzylideneindan-1,3-dione α-Oxide
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2-Phenyl-3,3,4,4-diphthaloyloxetane is formed when solutions of 2-benzylideneindan-1,3-dione α-oxide in benzene or carbon tetrachloride are heated, while 5-oxo-3-phenyl-2,2-phthaloyl-2,3-dihydroindenodioxine is formed when solutions in dioxane are heated.
- Anokhina, I. K.,Fedorova, N. G.,Zalukaev, L. P.,Krysin, M. Yu.
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p. 721 - 724
(2007/10/02)
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- Quinones. Part 11. The Reaction of o-Aminothiophenol with o-Benzo- and o-Naphtho-quinones: A New Route to 1H-Phenothiazin-1-ones
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1H-Phenothiazin-1-ones can be obtained by the condensation of o-aminothiophenol with 3,5-di-t-butyl- and 3-t-butyl-5-phenyl-o-benzoquinones.In the absence of large blocking groups the phenothiazinones are unstable.A methyl group at C-4 leads via the quinone-methide tautomer, to formation of a spiro-dimer the crystal structure of which was determined by X-ray analysis.By further reaction with o-aminothiophenol, 1H-phenothiazin-1-ones yield triphenodithiazines (benzothiazinophenothiazines). o-Naphthoquinones do not form benzo-1H-phenothiazin-1-ones with o-aminothiophenol.The parent compound yields 4-hydroxy-3H-benzophenothiazin-3-one by initial thiol addition at C-4 followed by rearrangement.
- Mackenzie, Neil E.,Surendrakumar, Sivagnanasundram,Thomson, Ronald H.,Cowe, Heather J.,Cox, Philip J.
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p. 2233 - 2242
(2007/10/02)
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