Exploring the Antibacterial and Antiparasitic Activity of Phenylaminonaphthoquinones-Green Synthesis, Biological Evaluation and Computational Study.

Organic compounds with antibacterial and antiparasitic properties are gaining significance for biomedical applications. This study focuses on the solvent-free synthesis (green synthesis) of 1,4-naphthoquinone or 2,3-dichloro-1,4-naphthoquinone with different phenylamines using silica gel as an acid solid support. The study also includes in silico PASS predictions and the discovery of antibacterial and antiparasitic properties of phenylaminonaphthoquinone derivatives -, which can be further applied in drug discovery and development.

Discovery of New 2-Phenylamino-3-acyl-1,4-naphthoquinones as Inhibitors of Cancer Cells Proliferation: Searching for Intra-Cellular Targets Playing a Role in Cancer Cells Survival.

A series of 2-phenylamino-3-acyl-1,4-naphtoquinones were evaluated regarding their in vitro antiproliferative activities using DU-145, MCF-7 and T24 cancer cells. Such activities were discussed in terms of molecular descriptors such as half-wave potentials, hydrophobicity and molar refractivity. Compounds and displayed the highest antiproliferative activity against the three cancer cells and were therefore further investigated.

Disparities Influencing Functional Outcomes Between Rural and Urban Patients With Acute Stroke.

Introduction: There is scarce information in Latin America about factors related to stroke patient outcomes in rural areas compared to urban ones.

Objective: To evaluate functional outcomes of stroke code patients from rural and urban areas and their relationship with socioeconomic disparity.

Methods: Prospective cohort study included patients of urban, semi-urban, and rural origin with stroke code from a high complexity hospital in southwestern Colombia between 2018 and 2019.

Antifungal Activity and In Silico Studies on 2-Acylated Benzo- and Naphthohydroquinones.

The high rates of morbidity and mortality due to fungal infections are associated with a limited antifungal arsenal and the high toxicity of drugs. Therefore, the identification of novel drug targets is challenging due to the several resemblances between fungal and human cells. Here, we report the in vitro antifungal evaluation of two acylphenols series, namely 2-acyl-1,4-benzo- and 2-acyl-1,4-naphthohydroquinones.

A dataset with complete geographic distributions of eight zonal monospecific forest types in mainland Spain.

Distribution area and surface are both parameters of paramount importance for habitat management, monitoring and conservation. Here we present the distribution of eight zonal forest types of mainland Spain that are consistent with the Habitat Types (HT) listed in Annex I of the European Union Habitats Directive 92/43 EC. Their dominant species and HT codes are (9120, 9130 and 9150), and (9230), (9330), (9430), ssp.

New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis and Antiproliferative Activities on Breast and Prostate Human Cancer Cells.

The reaction of 2-acyl-1,4-naphthoquinones with ,-dimethylaniline and 2,5-dimethoxyaniline, promoted by catalytic amounts of CeCl·7HO under "open-flask" conditions, produced a variety of 2-acyl-3-aminophenyl-1,4-naphthoquinones structurally related to the cytotoxic 2-acetyl-3-phenyl-1,4-naphthoquinone, an inhibitor of the heat shock chaperone protein Hsp90. The members of the 2-acyl-3-aminophenyl-1,4-naphthoquinone series were isolated in good yields (63-98%). The cyclic voltammograms of the 2-acyl-3-aminophenyl-1,4-naphthoquinone exhibit two one-electron reduction waves to the corresponding radical-anion and dianion and two quasireversible oxidation peaks.

Automatic Gait Phases Detection in Parkinson Disease: A Comparative Study.

Background: Parkinson's disease (PD) is a chronic condition that can be diagnosed and monitored by evaluating changes in the gait and arm movement parameters. In the gait movement, each cycle consists of two phases: stance and swing. Using gait analysis techniques, it is possible to get spatiotemporal variables derived from both phases.

Wristbands Containing Accelerometers for Objective Arm Swing Analysis in Patients with Parkinson's Disease.

In patients with Parkinson's disease (PD), arm swing changes are common, even in the early stages, and these changes are usually evaluated subjectively by an expert. In this article, hypothesize that arm swing changes can be detected using a low-cost, cloud-based, wearable, sensor system that incorporates triaxial accelerometers. The aim of this work is to develop a low-cost, assistive diagnostic tool for use in quantifying the arm swing kinematics of patients with PD.

Saturdays-in-Motion: Education and Empowerment through an Interdisciplinary Team Approach for Parkinson's Disease in Cali-Colombia.

Introduction: Parkinson's disease (PD) is one of the most prevalent age-related neurodegenerative disorders. The progression of PD produces an important disease burden in patients due to functional impairment, which also has repercussions on caregivers. In addition, it has become a challenge for health systems, especially in developing countries, which have limited resources.

In Vitro Inhibition of Hsp90 Protein by Benzothiazoloquinazolinequinones Is Enhanced in The Presence of Ascorbate. A Preliminary In Vivo Antiproliferative Study.

A series of benzo[]benzothiazolo[2,3-]quinazoline-7,12-quinones were prepared from 2-acylnaphthohydroquinones and 2-aminobenzothiazoles and were evaluated for their in vitro antiproliferative activity. After screening using the MTT reduction assay, their IC values were calculated on a panel of cancer cells (T24, DU-145, MCF-7). Current standard anticancer drugs were included as control, and their calculated IC values were 7.

Green Synthesis and Electrochemical Properties of Mono- and Dimers Derived from Phenylaminoisoquinolinequinones.

In the search for new quinoid compounds endowed with potential anticancer activity, the synthesis of novel heterodimers containing the cytotoxic 7-phenylaminoisoquinolinequinone and 2-phenylaminonaphthoquinone pharmacophores, connected through methylene and ethylene spacers, is reported. The heterodimers were prepared from their respective isoquinoline and naphthoquinones and 4,4'-diaminodiphenyl alkenes. The access to the target heterodimers and their corresponding monomers was performed both through oxidative amination reactions assisted by ultrasound and CeCl·7HO catalysis "in water".

Inhibition of and FtsZ Polymerization and Growth by Dihydroxynaphtyl Aryl Ketones.

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 , 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 proteins at the division site.

Half-Wave Potentials and In Vitro Cytotoxic Evaluation of 3-Acylated 2,5-(phenylamino)-1,4-benzoquinones on Cancer Cells.

A broad range of 3-acyl-2,5-(phenylamino)-1,4-benzoquinones were synthesized and their voltammetric values, as well as in vitro cancer cell cytotoxicities, were assessed. The members of this series were prepared from acylbenzoquinones and phenylamines, in moderate to good yields (47-74%), through a procedure involving a sequence of two in situ regioselective oxidative amination reactions. The cyclic voltammograms of the aminoquinones exhibit two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks.

Inhibition of Growth by Redox Cycling Phenylaminojuglones.

Infection by increases 10 times the risk of developing gastric cancer. Juglone, a natural occurring 1,4-naphthoquinone, prevents growth by interfering with some of its critical metabolic pathways. Here, we report the design, synthesis, and evaluation of a series of juglone derivatives, namely, 2/3-phenylaminojuglones, as potential growth inhibitors.

Preparation of Novel Homodimers Derived from Cytotoxic Isoquinolinequinones. A Twin Drug Approach.

The synthesis of five novel homodimers is reported based on the anilinoisoquinolinequinone scaffold. In these twin-drug derivatives, two units of the anilinoquinone pharmacophores are linked through a methylene spacer. The formation of dimers was achieved by reaction of isoquinolinequinones with 4, 4'-diaminodiphenylmethane via a sequence of two oxidative amination reactions.

Access to New Cytotoxic Quinone-Amino Acid Conjugates Linked through A Vinylic Spacer from 2-Acylnaphthoquinones and Methyl 3-Aminocrotonate.

The reaction of 2-acetyl- and 2-benzoyl-1,4-naphthoquinone with ()-methyl 3-(hydroxymethyl)aminocrotonate proceeds through a formal [3+3] process to yield the corresponding 1,2-dihydrobenzisoquinolinequinones in 63% and 72% yield, respectively. The reactions of 2-acyl-1,4-naphthoquinone with enaminones, derived from diverse l- and d-amino acid methyl esters, produced the corresponding naphthoquinone amino acids conjugates bonded through a vinyl spacer in the yields range 40-71%. The presence of not-separable isomers of the naphthoquinone amino acids conjugates in the ¹H- and C-NMR spectra is explained by the existence of conformational isomers generated by hindered rotation of the substituent bonded to the quinone double bond.

Targeting Akt as strategy to kill cancer cells using 3-substituted 5-anilinobenzo[c]isoxazolequinones: A preliminary study.

Several new 3-substituted 5-anilinobenzo[c]isoxazolequinones were synthesized from 1,4-benzoquinone and alkyl- or arylcarbaldehydes by a three-step synthetic sequence. The new compounds (3a-h) were tested in vitro in normal human fibroblasts and two cancer cell lines for their cytotoxic activity. The range of IC values obtained for the compounds was from 3.

Modulatory Effect of 2-(4-Hydroxyphenyl)amino-1,4-naphthoquinone on Endothelial Vasodilation in Rat Aorta.

The vascular endothelium plays an essential role in the control of the blood flow. Pharmacological agents like quinone (menadione) at various doses modulate this process in a variety of ways. In this study, , a 2-phenylamino-1,4-naphthoquinone derivative, significantly increased oxidative stress and induced vascular dysfunction at concentrations that were not cytotoxic to endothelial or vascular smooth muscle cells.

Synthesis and Cytotoxic Activity on Human Cancer Cells of Novel Isoquinolinequinone-Amino Acid Derivatives.

A variety of aminoisoquinoline-5,8-quinones bearing α-amino acids moieties were synthesized from 3-methyl-4-methoxycarbonylisoquinoline-5,8-quinone and diverse l- and d-α-amino acid methyl esters. The members of the series were evaluated for their cytotoxic activity against normal and cancer cell lines by using the (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (MTT) assay. From the current investigation, structure-activity relationships demonstrate that the location and structure of the amino acid fragment plays a significant role in the cytotoxic effects.

In vivo inhibition of tumor progression by 5 hydroxy-1,4-naphthoquinone (juglone) and 2-(4-hydroxyanilino)-1,4-naphthoquinone (Q7) in combination with ascorbate.

The purpose of the study was to obtain further in vivo data of antitumor effects and mechanisms triggered by juglone and Q7 in combination with ascorbate. The study was done using Ehrlich ascites tumor-bearing mice. Treatments were intraperitoneal every 24 h for 9 days.

Binding of dihydroxynaphthyl aryl ketones to tubulin colchicine site inhibits microtubule assembly.

Dihydroxynaphthyl aryl ketones 1-5 have been evaluated for their abilities to inhibit microtubule assembly and the binding to tubulin. Compounds 3, 4 and 5 displayed competitive inhibition against colchicine binding, and docking analysis showed that they bind to the tubulin colchicine-binding pocket inducing sheets instead of microtubules. Remarkable differences in biological activity observed among the assayed compounds seem to be related to the structure and position of the aryl substituent bonded to the carbonyl group.

DNA damage and inhibition of akt pathway in mcf-7 cells and ehrlich tumor in mice treated with 1,4-naphthoquinones in combination with ascorbate.

The aim of this study was to enhance the understanding of the antitumor mechanism of 1,4-naphthoquinones and ascorbate. Juglone, phenylaminonaphthoquinone-7, and 9 (Q7/Q9) were evaluated for effects on CT-DNA and DNA of cancer cells. Evaluations in MCF-7 cells are DNA damage, ROS levels, viability, and proliferation.

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light "on water".

A number of N-phenyl-1,4-naphthoquinone monoimines 6-10 were prepared by on-water oxidative phenylamination of 1,5-dihydroxynaphthalene (1) and 5-acetylamino-1-hydroxynaphthalene (5) with oxygen-substituted phenylamines under aerobic conditions and either solar or green LED radiation, in the presence of rose bengal as singlet oxygen sensitizer. As compared to the conventional oxidative phenylamination procedures, this novel synthetic method offers the advantage of aerobic conditions "on water" instead of hazardous oxidant reagents currently employed in aqueous alcoholic media.

Substituted 3‑acyl‑2‑phenylamino‑1,4‑naphthoquinones intercalate into DNA and cause genotoxicity through the increased generation of reactive oxygen species culminating in cell death.

Naphthoquinones interact with biological systems by generating reactive oxygen species (ROS) that can damage cancer cells. The cytotoxicity and the antitumor activity of 3‑acyl‑2‑phenylamino‑1,4‑naphthoquinones (DPB1‑DPB9) were evaluated in the MCF7 human breast cancer cell line and in male Ehrlich tumor‑bearing Balb/c mice. DPB4 was the most cytotoxic derivative against MCF7 cells (EC50 15 µM) and DPB6 was the least cytotoxic one (EC50 56 µM).