Eco-Friendly Synthesis and Antiproliferative Evaluation of Some Oxygen Substituted Diaryl Ketones

Arenas, Paola; Pena, Andrés; Ríos, David; Benites, Julio; Muccioli, Giulio G.; Calderón, Pedro Buc; Valderrama, Jaime A.

doi:10.3390/molecules18089818

Cited by 20 publications

(13 citation statements)

References 48 publications

(54 reference statements)

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“…Compound 3a and 4a were prepared from 2,5-dihydroxybenzaldehyde ( 1a ) and enaminones 2a,b respectively, by using a previously reported one-pot procedure [16,17,18]. Through the same procedure, compounds 3b – d and 4b – d were accomplished from the corresponding acylhydroquinones 1b – d [19,20] and enaminones (Table 1). 4-Aminopent-3-en-2-one ( 2b ) was prepared in 80% from acetyl acetone and ammonium carbamate according to the method reported by Litvié et al [21].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones

et al. 2014

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Abstract:The synthesis of a variety of 1-aryl-7-phenylaminoisoquinolinequinones from 1,4-benzoquinone and arylaldehydes via the respective 1-arylisoquinolinequinones is reported. The cyclic voltammograms of the new compounds exhibit two one-electron reduction waves to the corresponding radical-anion and dianion and two quasi-reversible oxidation peaks. The half-wave potential values (E I ½ ) of the members of the series have proven sensitive to the electron-donor effect of the aryl group (phenyl, 2-thienyl, 2-furyl) at the 1-position as well as to the phenylamino groups (anilino, p-anisidino) at the 7-position. The antiproliferative activity of the new compounds was evaluated in vitro using the MTT colorimetric method against one normal cell line (MRC-5 lung fibroblasts) and two human cancer cell lines: AGS human gastric adenocarcinoma and HL-60 human promyelocytic leukemia cells in 72-h drug exposure assays. Among the series, compounds 5a, 5b, 5g, 5h, 6a and 6d exhibited interesting antiproliferative activities against human gastric adenocarcinoma. The 1-arylisoquinolinequinone 6a was found to be the most promising active compound against the tested cancer cell lines in terms of IC50 values 727(1.19; 1.24 µM) and selectivity index (IS: 3.08; 2.96), respect to the anti-cancer agent etoposide used as reference (IS: 0.57; 0.14).

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Section: Resultsmentioning

confidence: 99%

Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones

et al. 2014

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“…Compounds 1–4 were prepared from 1,4-naphthoquinone and the corresponding aldehydes: thiophene-2-carbaldehyde; thiophene-3-carbaldehyde; furan-2-carbaldehyde; and 1H-pyrrole-2-carbaldehyde (Benites et al, 2011). The structure of compounds 1–4 was confirmed by 1 H, 13 C NMR spectra (Arenas et al, 2013). Compound 5 was prepared from 1,4-naphthoquinone and 3,4,5-trimethoxybenzaldehyde, and the spectral data were in agreement with those reported in the literature (Iribarra et al, 2012).…”

Section: Methodsmentioning

confidence: 93%

Inhibition of Escherichia coli and Bacillus subtilis FtsZ Polymerization and Bacillus subtilis Growth by Dihydroxynaphtyl Aryl Ketones

et al. 2019

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The increasing detection of virulent and/or multidrug resistant bacterial strains makes necessary the development of new antimicrobial agents acting through novel mechanisms and cellular targets. A good choice are molecules aimed to interfere with the cell division machinery or divisome , which is indispensable for bacterial survival and propagation. A key component of this machinery, and thus a good target, is FtsZ, a highly conserved GTPase protein that polymerizes in the middle of the cell on the inner face of the cytoplasmic membrane forming the Z ring, which acts as a scaffold for the recruitment of the divisome proteins at the division site. In this work, we tested the inhibitory effect of five diaryl naphtyl ketone (dNAK) molecules on the in vitro polymerization of both Escherichia coli and Bacillus subtilis FtsZ (EcFtsZ and BsFtsZ, respectively). Among these compounds, dNAK 4 showed the strongest inhibition of FtsZ polymerization in vitro , with an IC 50 of 2.3 ± 0.06 μM for EcFtsZ and 9.13 ± 0.66 μM for BsFtsZ. We found that dNAK 4 binds to GDP-FtsZ polymers but not to the monomer in GTP or GDP state. This led to the polymerization of short and curved filaments, rings, open rings forming clusters, and in the case of BsFtsZ, a novel cylindrical structure of stacked open rings. In vivo , dNAK 4 had almost no effect on the growth of E. coli in liquid culture, in contrast to the strong inhibitory effect observed over B. subtilis growth. The insensitivity of E. coli to this compound is probably related to the impermeability of dNAK 4 to the outer membrane. The low amount of this compound required to inhibit several of the bacterial strains tested and the lack of a cytotoxic effect at the concentrations used, makes dNAK 4 a very good candidate as a starting molecule for the development of a new antibiotic.

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“…The mixture was irradiated for six days (total illumination time of 30 h), under solar radiation conditions in the range 800-1100 Watts/m 2 (December-March) [5]. The mixture reaction was chromatographed on silica gel (3:1 petroleum ether/ethyl acetate) to give pure with graphite-monochromated MoKα radiation ( 0.71073Å .…”

Section: Methodsmentioning

confidence: 99%

Crystal Structure of (1,4-Dihydroxynaphthalen-2-Yl) (4'-Methoxyphenyl) Methanone

Benites

Valderrama

Ríos

et al. 2016

J. Chil. Chem. Soc.

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Eco-Friendly Synthesis and Antiproliferative Evaluation of Some Oxygen Substituted Diaryl Ketones

Cited by 20 publications

References 48 publications

Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones

Synthesis, Half-Wave Potentials and Antiproliferative Activity of 1-Aryl-substituted Aminoisoquinolinequinones

Inhibition of Escherichia coli and Bacillus subtilis FtsZ Polymerization and Bacillus subtilis Growth by Dihydroxynaphtyl Aryl Ketones

Crystal Structure of (1,4-Dihydroxynaphthalen-2-Yl) (4'-Methoxyphenyl) Methanone

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