1,2-dihydroxy-3-methyl-anthracene-9,10-dione

Synthesis of 2-acetyl-1,4-dimethoxynaphthalene, a potential intermediate for disubstituted naphtho[2,3,c]pyran-5,10-dione.[Pubmed:24689294]

Nat Prod Commun. 2014 Feb;9(2):217-8.

2-Acetyl-1-hydroxynaphthalene was converted into the title compound in three steps (bromination, substitution and methylation). 1-Methoxynaphthalene on bromination, substitution and acetylation, respectively, also yielded the target compound.

Synthesis of 1,4-anthracene-9,10-dione derivatives and their regulation of nitric oxide, IL-1beta and TNF-alpha in activated RAW264.7 cells.[Pubmed:23819539]

Chem Biol Drug Des. 2013 Oct;82(4):463-7.

Mitoxantrone is an anthracenedione antineoplastic and immunosuppressive agent approved for multiple sclerosis treatment. Novel mono- and disubstituted anthraquinone derivatives, analogues of mitoxantrone, were synthesized through the addition of lipophilic amino alcohols and evaluated for their effect on IL-1beta, TNF-alpha and nitric oxide production by LPS/IFN-gamma-stimulated RAW264.7 cells. The disubstituted 1,4-anthracene-9,10-dione 10 showed significant inhibition of nitric oxide, TNF-alpha and IL-1beta production at the concentration of 5 mug/mL, with a much lower cytotoxicity than mitoxantrone. The monosubstituted 3, 4, 11, 12 and 13 also displayed a moderate to good inhibitory capacity on IL-1beta production. However, the methylated compounds 11, 12 and 13 failed to inhibit the TNF-alpha production, and compound 13 was the only one to decrease the production of nitric oxide. None of these derivatives was toxic at the tested concentrations. Compounds 10 and 13 had better inhibitory capacity of the inflammatory mediators analyzed, with reliable viability of the cells.

Spectroscopic studies of 1,4-dimethoxy-2,3-dimethylanthracene-9,10-dione on plasmonic silver nanoparticles.[Pubmed:24973788]

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Dec 10;133:472-9.

Silver nanoparticles (Ag NPs) of different sizes from 7nm to 22nm have been prepared by simple Dirk and Charles chemical method and characterized using UV-vis spectroscopy and high resolution transmission electron microscopy (HRTEM). Fluorescence quenching of 1,4-dimethoxy-2,3-dimethylanthracene-9,10-dione (DMDMAD) by silver nanoparticles has been investigated by fluorescence spectroscopy to understand the role of quenching mechanism. Furthermore, the intensity of DMDMAD fluorescence emission peak decreases with decrease in the size of the Ag NPs. The fluorescence quenching rate constant and association constant for above system were determined using Stern-Volmer and Benesi-Hildebrand plots. The mechanism of DMDMAD fluorescence quenched by Ag NPs was discussed according to the Stern-Volmer equation. It has been observed that the quenching due to Ag NPs proceeds via dynamic quenching process. The distance between DMDMAD (donor) to Ag NPs (acceptor) and the critical energy transfer distance were estimated based on the Forster Resonance Energy Transfer (FRET) theory.

Spectroscopic (FT-IR, FT-Raman), first order hyperpolarizability, NBO analysis, HOMO and LUMO analysis of 2,4-bis(2-methoxyphenyl)-1-phenylanthracene-9,10-dione by ab initio HF and density functional methods.[Pubmed:24012980]

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 3;117:413-21.

Anthraquinone derivatives are most important class of a system that absorb in the visible region. In this work, the vibrational spectral analysis was carried out using FT-IR and FT-Raman spectroscopy for 2,4-bis(2-methoxyphenyl)-1-phenylanthracene-9,10-dione. Theoretical calculations were performed by ab initio HF and DFT methods using 6-31G(*) basis set. The complete vibrational assignments of wavenumbers were made on the basis of potential energy distribution. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The calculated geometrical parameters (DFT) are in agreement with that of similar derivatives. The calculated first hyperpolarizability of the title compound is 4.69x10(-30) esu, which is 36.08 times that of urea and the title compound and the series of compounds it represents are attractive candidates for further studies in non linear optical applications.