75112-65-1Relevant academic research and scientific papers
Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones
Leyva, Elisa,López, Lluvia I.,de la Cruz, Ramón F. García,Espinosa-González, Claudia G.
, p. 1813 - 1827 (2017/02/15)
Several synthetic and natural naphthoquinone derivatives have been associated with antifungal activity. Candida albicans is a fungus that is known to exist in the normal human flora, but under certain conditions it can cause mild to fatal infections. Its pathogenicity has been associated with fungus conversion from cellular yeast to filamentous form Y–M. Inhibition of this process by several anilino-, dianilino-, phenoxy-, and diphenoxy-1,4-naphthoquinones was investigated in order to find some correlation between structure, redox properties and biological activity.
Spectral and structural characterization of 2-(fluorophenylamino)- and 2-(nitrophenylamino)-1,4-naphthoquinone derivatives
Leyva, Elisa,Schmidtke Sobeck, Sarah J.,Loredo-Carrillo, Silvia E.,Magaldi-Lara, Diego A.
, p. 1 - 7 (2014/05/06)
Naphthoquinone amino derivatives exhibit interesting physicochemical properties and are of interest for potential medicinal purposes. The preparation of novel 2-(nitrophenylamino)-1,4-naphthoquinones derivatives was achieved by reaction of nitroanilines with 1,4-naphthoquinone with a catalytic amount of FeCl3 or by direct nitration of 2-(phenylamino)-1,4-naphthoquinone (PAN). Structural and photophysical properties of a series of NO2PANs and FPANs derivatives are examined using computational and spectroscopic methods. Absorbance and emission spectra are measured in a range of solvent environments to examine the impact of solvent-solute interactions. Additionally quantum calculations are used to evaluate the electronic nature of the spectral transitions and compare structures of the different PAN derivatives. The lowest energy electronic transitions have charge transfer character, and show the most sensitivity to solvent and substituents. Higher energy π- π* transitions are relatively insensitive to both factors. Computational predictions are in good agreement with the experimental spectra, and provide molecular-level insight variations amongst the different aniline-substituents.
General method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones (X = ferrocenyl, OMe, Me, I, Cl, and NO2) from 2-methoxy-1,4-naphthoquinone and investigation of H+ and Mg2+ catalysts with DFT calculations
Francisco, Acácio I.,Vargas, Maria D.,Carneiro, J. Walkimar de M.,Lanznaster, Maurício,Torres, José C.,Camara, Celso A.,Pinto, Angelo C.
experimental part, p. 228 - 232 (2009/04/13)
A rapid and simple method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones from 2-methoxy-1,4-naphthoquinone, in boiling MeOH, using MgCl2 and p-toluenesulfonic acid as catalysts is described. This methodology has been applied successfully to the synthesis of electron donor (4-OMe, 4-Me, 4-ferrocenyl) and electron withdrawing (4-I, 4-Cl, 4- and 3-NO2) aniline derivatives. The effect of both H+ and Mg2+ as catalysts was investigated using DFT calculations carried out at the B3LYP/6-31G(d) level. The electronic properties of the novel 2-(4-ferrocenylphenylene)amine-1,4-naphthoquinone 3b were investigated and show that the ferrocenyl and the methoxy group have similar electron donor properties in 2-(4-methoxy)amine-1,4-naphthoquinone 3a.
Quinone Chemistry. Reaction of 2,3-Dichloro-1,4-naphthoquinone with Arylamines in Pyridine
Agarwal, Nand L.,Schaefer, Wolfram
, p. 5139 - 5143 (2007/10/02)
2,3-Dichloro-1,4-naphthoquinone (1) reacts with arylamines (2) in pyridine to afford 2-(arylamino)-3-chloro-1,4-naphthoquinone (6), 2-(arylamino)-1,4-naphthoquinone (5), 2-(arylamino)-1,4-naphthoquinone-3-pyridinium perchlorate (4), and 2-amino-1,4-naphth
