363159-42-6Relevant academic research and scientific papers
2-Phenylaminonaphthoquinones and related compounds: Synthesis, trypanocidal and cytotoxic activities
Sieveking, Ivan,Thomas, Pablo,Estevez, Juan C.,Quinones, Natalia,Cuellar, Mauricio A.,Villena, Juan,Espinosa-Bustos, Christian,Fierro, Angelica,Tapia, Ricardo A.,Maya, Juan D.,Lopez-Munoz, Rodrigo,Cassels, Bruce K.,Estevez, Ramon J.,Salas, Cristian O.
, p. 4609 - 4620 (2014/10/15)
A series of new 2-aminonaphthoquinones and related compounds were synthesized and evaluated in vitro as trypanocidal and cytotoxic agents. Some tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity and selectivity as compared with current trypanocidal drug, nifurtimox. Compound 4l exhibit higher selectivity than nifurtimox against Trypanosoma cruzi in comparison with Vero cells. Some of the synthesized quinones were tested against cancer cells and normal fibroblasts, showing that certain chemical modifications on the naphthoquinone moiety induce and excellent increase the selectivity index of the cytotoxicity (4g and 10). The results presented here show that the anti-T. cruzi activity of 2-aminonaphthoquinones derivatives can be improved by the replacement of the benzene ring by a pyridine moiety. Interestingly, the presence of a chlorine atom at C-3 and a highly lipophilic alkyl group or aromatic ring are newly observed elements that should lead to the discovery of more selective cytotoxic and trypanocidal compounds.
Studies on the chemistry of 2-[3-(2-nitrophenyl)-2-oxopropyl]benzaldehydes: Novel syntheses of 5h-benzo[b]carbazole-6,11-diones and indolo[1,2-b] isoquinoline-6,11-diones
Fernandez, Marcos
experimental part, p. 3051 - 3060 (2009/12/29)
Syntheses of 5H-benzo[b]carbazole-6,11-diones and indolo[1,2-b] isoquinoline-6,11-diones are described. Both compounds are synthesized from 2-[3-(2-nitrophenyl)-2-oxopropyl]benzaldehydes, which were obtained from commercially available indan-1-ones in six
Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation
Allan, Kevin M.,Hong, Boram D.,Stoltz, Brian M.
supporting information; experimental part, p. 4960 - 4964 (2010/02/15)
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.
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
Barcia, José C,Cruces, Jacobo,Estévez, Juan C,Estévez, Ramón J,Castedo, Luis
, p. 5141 - 5144 (2007/10/03)
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.
Palladium mediated total synthesis of o-acetylphenylacetic acids: A general route to indolo[2,3-b]naphthalene-6,11-diones
Cruces, Jacobo,Estévez, Juan C,Castedo, Luis,Estévez, Ramón J
, p. 4825 - 4827 (2007/10/03)
Here we describe a new, efficient general synthesis of o-acetylphenylacetic acids by Heck palladium-catalyzed arylation of n-butyl vinyl ether with o-bromophenylacetic acids, and its application to the synthesis of indolo[2,3-b]naphthalene-6,11-diones.
A simple synthesis of benzocarbazolequinones via o-nitroarylation of 2- hydroxy-1,4-naphthoquinones
Kobayashi, Kazuhiro,Taki, Tetsuya,Kawakita, Masataka,Uchida, Masaharu,Morikawa, Osamu,Konishi, Hisatoshi
, p. 349 - 354 (2007/10/03)
The reaction of 2-hydroxy-1,4-naphthoquinones (1a-c) with o- fluoronitrobenzenes (2a,b) in the presence of K2CO3 in DMSO at 100 °C gave 2-hydroxy-3-(2-nitroaryl)-1,4-naphthoquinones (3a-e) in moderate to fair yields, which in turn we
