Margarita Gutiérrez

Margarita Gutiérrez
Universidad de Talca · Insitute of Chemestry of Natural Resources

About

116
Publications
26,237
Reads
How we measure 'reads'
A 'read' is counted each time someone views a publication summary (such as the title, abstract, and list of authors), clicks on a figure, or views or downloads the full-text. Learn more
1,196
Citations
Citations since 2016
43 Research Items
792 Citations
2016201720182019202020212022050100150
2016201720182019202020212022050100150
2016201720182019202020212022050100150
2016201720182019202020212022050100150

Publications

Publications (116)
Article
Full-text available
Pyrazole-fused phenanthroline compounds were obtained through several synthetic routes. NMR, HRMS, and IR techniques were used to characterize and confirm the chemical structures. Crystal structures were obtained from compounds 3a, 5b, 5j, 5k, and 5n and analyzed using X-ray diffraction. Compounds were evaluated as acetyl (AChE) and butyrylcholines...
Article
Alzheimer's disease (AD) is a degenerative neurological disease characterized by gradual loss of cognitive skills and memory. The exact pathogenesis involved still remains unrevealed, but several studies indicate the involvement of an array of different enzymes, underlining the multifactorial character of the disease. Inhibition of these enzymes is...
Article
Isocyanide-based multicomponent reactions turn out to be interesting synthetic strategies, with highly valued advantages such as atomic economy, selectivity, among others. Furthermore, Isocyanide-based multicomponent reactions have been shown to generate a wide range of products with significant biological activity. Recently, it has been described...
Article
Ethyl 4-(4-(dimethylamino)phenyl)-3,6-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (5) was synthesized according to our previously reported procedure in a 92% yield and crystallized by a slow evaporation technique. This report describes the in-depth structural analysis thereof. The structural characterization and purity of the title c...
Article
Full-text available
In an attempt to rationalize the search for new potential anti-inflammatory compounds on the COX-2 enzyme, we carried out an in silico protocol that successfully combines the prediction of physicochemical and pharmacokinetic properties, molecular docking, molecular dynamic simulation, and free energy calculation. Starting from a small library of co...
Article
In this study, we reported for the first time the crystalline and molecular structure of the compound N-(naphthalen-1-yl) -2- (piperidin-1-yl) acetamide. The synthesis of the compound was carried out by amidation using a coupling reagent (N, N'-diisopropylcarbodiimide) and subsequently amination. The compound was experimentally characterized by UV-...
Article
Crystalline organic compound, N-(4-acetylphenyl)quinoline-3-carboxamide (4) was readily prepared using our previously reported experimental procedure by the reaction of quinoline-3-carboxylic acid (1) with thionyl chloride to generate the acid chloride in situ followed by the coupling itself with 4-aminoacetophenone (3). This report describes the i...
Article
Background Adenosine is a natural nucleoside present in various organs and tissues, where it acts as a modulator of diverse physiological and pathophysiological processes. These actions are mediated by at least four G protein-coupled receptors, which are widely and differentially expressed in tissues. Interestingly, high concentrations of adenosine...
Conference Paper
Full-text available
Advances in different technological and scientific fields have led to the development of tools that allow the design of drugs in a rational way, using defined therapeutic targets, and through simulations that offer a molecular view of the ligand–receptor interactions, giving precise information for the design and synthesis of new compounds. Ion cha...
Article
Full-text available
A series of 44 hybrid compounds that included in their structure tetrahydroquinoline (THQ) and isoxazole/isoxazoline moieties were synthesized through the 1,3-dipolar cycloaddition reaction (1,3-DC) from the corresponding N-allyl/propargyl THQs, previously obtained via cationic Povarov reaction. In vitro cholinergic enzymes inhibition potential of...
Article
Full-text available
In this work, we present results about the synthesis and the antioxidant properties of seven adenosine derivatives. Four of these compounds were synthesized by substituting the N6-position of adenosine with aliphatic amines, and three were obtained by modification of the ribose ring. All compounds were obtained in pure form using column chromatogra...
Article
Full-text available
A series of pyrazolo-fused 4-azafluorenones (indeno[1,2-b]pyrazolo[4,3-e]pyridines, IPP) were synthesized via the three-component reaction between arylaldehydes, 3-methyl-1H-pyrazol-5-amine and 1,3-indanedione in an ionic liquid as a catalyst at room temperature. The applied synthetic route has the advantages of easy work-up under mild reaction con...
Article
Full-text available
New N-propargyl tetrahydroquinolines 6a-g have been synthesized efficiently through the cationic Povarov reaction (a domino Mannich/Friedel-Crafts reaction), catalyzed by Indium (III) chloride (InCl3), from the corresponding N-propargylanilines preformed, formaldehyde and N-vinylformamide, with good to moderate yields. All tetrahydroquinoline deriv...
Article
Full-text available
The chalcone and bis-chalcone derivatives have been synthesized under sonication conditions via Claisen-Schmidt condensation with KOH in ethanol at room temperature (20-89%). The structures were established on the basis of NMR, IR, Single-crystal XRD, and MS. The best compound 3u had inhibitory activity (IC 50 = 7.50 µM). The synthesis, the antioxi...
Article
Full-text available
The imino‐Diels‐Alder reaction is one of the most common strategies in organic chemistry and is an important tool for providing a broad spectrum of biologically active heterocyclic systems. A combined theoretical and experimental study of the imino‐Diels‐Alder reaction is described. The new phenanthroline‐tetrahydroquinolines were evaluated as chol...
Article
Full-text available
Background Eugenol is a phenolic compound with a wide spectrum of biological activities such as antibacterial and antioxidant. Objective Eugenol is an ideal candidate as a natural antioxidant additive, especially for those substances that are affected by lipoperoxidation process, this is the case of essential oils that have an important role in th...
Article
2-bromo-N-(2,4-difluorobenzyl)benzamide was synthesized in 92% yield by the reaction of commercial 2-bromobenzoic acid with (2,4-difluorophenyl)methanamine. The new ti- tle compound was characterized by 1 H and 13 C NMR, EI-MS and FT-IR. The crystal struc- ture was stablished by single-crystal X-ray diffraction analysis. The colorless plates crys-...
Article
Full-text available
This is the first Call for Xth International Symposium on Natural Products Chemistry and its Applications, to be held in Grand Hotel Termas de Chillan, Chillan Chile, 25-29 Nov. 2019
Article
In recent years, the design, development, and evaluation of several inhibitors of the BACE1 enzyme, as part of Alzheimer's treatment, have gathered the scientific community's interest. Here, a linear regression model was built using binding free energy calculations through the Bennett acceptance ratio method for 20 known inhibitors of the BACE1 enz...
Article
Alzheimer's disease (AD) is the most prevalent neurodegenerative disease, presenting the most devastating consequences on human health and life quality. Coumarin‐quinoline hybrids were synthesized following a very efficient and versatile strategy. Small structural variations contributed to dual acetyl/butyrylcholinesterases (AChE/BuChE) activity or...
Article
Full-text available
Ugi four component reaction (Ugi-4CR) isocyanide-based multicomponent reactions were used to synthesize diN-substituted glycyl-phenylalanine (diNsGF) derivatives. All of the synthesized compounds were characterized by spectroscopic and spectrometric techniques. In order to evaluate potential biological applications, the synthesized compounds were t...
Article
Full-text available
Keeping in mind the concept of green chemistry, this research aims to synthesize and characterize new ionic liquids (ILs) derived from N-cinnamyl imidazole with different sizes of alkyl chains (1, 6, 8, and 10 carbon atoms), and evaluate their antibacterial activity against Skin and soft tissue infections (SSTIs) causative bacteria. The antibacteri...
Article
Full-text available
Since 1929, several researchers have conducted studies in relation to the nucleoside of adenosine (1) mainly distribution identifying, characterizing their biological importance and synthetic chemistry to which this type of molecule has been subjected to obtain multiple of its derivatives. The receptors that interact with adenosine and its derivati...
Article
Given the wide spectrum of biological uses of pyrazolo[1,5-c]quinazoline and spiro-quinazoline derivatives as anticancer, anti-inflammatory analgesic agents, and their therapeutic applications in neurodegenerative disorders, it is compulsory to find easy, efficient, and simple methods to obtain and chemically diversify these families of compounds,...
Article
Full-text available
An efficient route for the synthesis of novel 7-aryl and 7-spiropyrazolo[4\(^{\prime }\),3\(^{\prime }\):5,6]pyrido[2,3-d]pyrimidine derivatives is described. These compounds were obtained by a cyclocondensation reaction between pyrazolopyridinediamines 4 and aldehydes 5 or cyclic ketones 6 in the presence of acetic acid as catalyst. This procedure...
Article
Full-text available
Pyrazolo[3,4- b ]pyridines derivatives have been synthesized via one-pot condensation of 3-methyl-1-phenyl-1 H -pyrazolo-5-amine ( 1 ), paraformaldehyde ( 2 ) and β-diketones ( 3 ) under microwave irradiation in aqueous media catalyzed by InCl 3 .
Article
Full-text available
An amide chalcone has been synthesized in a two-step reaction. First, N-(4-acetylphenyl) quinoline-3-carboxamide 2 was synthesized by the reaction of quinoline-3-carboxylic acid 1 and thionyl chloride (SOCl 2), following the addition of 4-aminoacetophenone. Then, a typical Claisen-Schmidtreactionwas made between 2 and piperonal using KOH solution a...
Article
Full-text available
Given the broad spectrum of biological uses of heteroaryl-acrylonitrile derivatives, it is necessary to find simple methods to synthesize and diversify this family of compounds. We report a stereoselective synthesis of a series of new (E) -2-(1 H -indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles (3a – 3i) obtained from 3-(cyanoacetyl)indole and het...
Article
Full-text available
The aim of the present investigation was to appraise variation in the chemical composition and antimicrobial activity against phytopatogenic bacterial of essential oils from Azorella spinosa. Three samples of A. spinosa were collected in different date in the same area. The essential oils were obtained for hydro-destillation using a Clevenger-type...
Book
Full-text available
PROCEEDINGS OF IX INTERNATIONAL SYMPOSIUM ON NATURAL PRODUCTS CHEMISTRY AND ITS UTILIZATION, CHILLAN-CHILE, NOV 2016
Article
Full-text available
A small series of tetrahydroindazoles was prepared, starting from 2-acetylcyclohexanone and different hydrazines using reflux and a focused microwave reactor. Microwave irradiation (MW) favored the formation of the desired products with improved yields and shortened reaction times. This is a simple and green method for the synthesis of substituted...
Article
Full-text available
New N-allyl/propargyl 4-substituted 1,2,3,4-tetrahydroquinolines derivatives were efficiently synthesized using acid-catalyzed three components cationic imino Diels–Alder reaction (70–95%). All compounds were tested in vitro as dual acetylcholinesterase and butyryl-cholinesterase inhibitors and their potential binding modes, and affinity, were pred...
Article
Full-text available
C15H9N3S, triclinic, P-1 (no. 2), a = 9.5737(5) Å, b = 12.0958(4) Å, c = 12.2705(7) Å, α = 64.083(5) Å, β = 80.907(4) Å, γ = 82.800(4), V = 1259.44(11) Å3 , Z = 4, Rgt(F) = 0.0460, wRref(F2) = 0.140, T = 293(2) K.
Article
Full-text available
Alzheimer disease (AD) is a neurodegenerative disorder that causes damages in brain due to factors such as oxidative stress, low-levels of the neurotransmitter acetylcholine, β-amyloid protein aggregation, etc. It is necessary the design of novel efficient drugs for AD treatment to counteract the increase of people suffering from AD. Recently, hete...
Article
Novel 6-methyl-3-carboxamidocoumarins (compounds 4-15) were synthesized by an effective three step synthetic strategy and screened towards MAO, AChE and BuChE enzymes. In general, the compounds act as selective MAO-B inhibitors. Compound 11 is highlighted as a potent (IC50hMAO-B = 4.66 nM), reversible and non-competitive MAO-B inhibitor.
Article
Natural cholinesterase inhibitors have been found in many biological sources. Nine compounds with agarofuran (epoxyeudesmane) skeletons were isolated from seeds and aerial part of Maytenus disticha and Euonymus japonicus. The identification and structural elucidation of compounds were based on spectroscopic data analyses. All compounds had inhibito...
Poster
Full-text available
Azorella spinosa is a species belonging to the genus Azorella of the Apiaceae Family, and is widely it is distributed in the Andean-Patagonian region from Costa Rica to southern Chile and Argentina, and a potential source of bioactive compounds with various diterpenoids structures of type azorellane, yaretane and mulinanes, exhibiting a wide range...
Article
Full-text available
The objective of this study was to investigate the inhibition of antibacterial and antioxidant activity by extracts of the aerial parts of Azorella multifida collected in Cuenca, Ecuador. Azorella multifida presented poor antioxidant activity in dichloromethane and petroleum ether extracts (DPPH) with IC 50 values >300 ug/mL, while it showed modera...
Article
Full-text available
Phytochemical investigation of Azorella madreporica led to the isolation of four known compounds and an unknown chalcone. The structure of the new compound was identified by spectroscopy, including two-dimensional NMR techniques and comparison with published spectral data. The antioxidant activity of chalcone (compound 1) was measured using the 1,2...
Article
The inhibition of the degradation of acetylcholine by cholinesterases (ChE) is one of the main targets for the treatment of Alzheimer disease (AD). In the present work, a new series of coumarin-quinoline hybrids were efficiently synthesized and evaluated as inhibitors against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), using the...
Article
Full-text available
For the first time, the adsorption of pesticides such as azinphos-methyl and methamidophos by polyamidoamine (PAMAM) derivatives was studied. Amine groups of PAMAM (G4 and G5) were functionalized with different biomolecules such as folic acid, coumarine, arginine, lysine, and asparagine. Subsequently, the synthesized compounds were used to trap org...
Article
A series of tetrahydroquinolines (Compounds 1-8) were synthesized using Povarov reactions, subsequently characterized using spectroscopic methods and evaluated as Acetylcholinesterase/Butirylcholinesterase inhibitors. Bioinformatics tools analyzed active site interactions, leading to the design of a more active new compound. The most potent compoun...
Article
Full-text available
Adenosine is an endogenous nucleoside distributed throughout the body and is recognized electrophysiological effects since 1929. For its part, adenosine analogs and conjugates are of great importance and have multiple applications as drugs for cardiovascular, immune therapy and other diseases. In addition, the receptors that interact with adenosine...
Article
Nitrogen heterocycles are a part of a special group of organic substances found in many biologically active natural and synthetic products with properties pharmacologically relevant. The synthesis and spectroscopic characterization of tetrahydroquinolines (THQs) and isoxazole are shown. These compounds were evaluated for their in vitro antibacteria...
Article
Recent evidence suggests that the alpha7 nicotinic acetylcholine receptors (alpha7 nAChRs) participate in the development of angiogenesis and could be a new endothelial target for revascularization in therapeutic angiogenesis. It has been shown that in human umbilical vein endothelial cells (HUVECs) alpha7 nAChR agonists increase the intracellular...
Article
Full-text available
Members of the family Cyperaceae such as Cyperus alopecuroides, Cyperus articulatus, Cyperus scariosus and Cyperus rotundus possess significant amount of studies about their antioxidant activities and other properties. Nevertheless, the plant Cyperus digitatus belonging to the genus Cyperus lacks of studied about any kind of intrinsic activity. Dif...
Article
Two new diterpenes,2-acetoxy-13-hydroxy-mulin-11-ene and 2-acetoxy-mulin-11, 13-diene,have been isolated from the aerial parts of Azorella spinosa and their structures determined by spectroscopic and conventional chemical methods. Furthermore, 2, 13-dihydroxy-mulin-11-ene was obtained using a basic hydrolysis of the first compound. Two diterpenes r...
Article
Full-text available
Herein, we report the synthesis of new substituted 3-(2-chloroquinolin-3-yl)-5-phenylisoxazole (3a-j) by click chemistry in good to moderate yields. This approach is based on the regioselective copper(I)-catalyzed cycloaddition between different nitrile oxides derived from 2-chloroquinoline-3- carbaldehyde (2a-j) and phenylacetylene. Finally these...
Article
Full-text available
Alperujo is a combination of liquid and solid waste of olive oil processing, being dangerous for the environment. This residual does not have common commercial interest, and companies usually dispose of it in landfills where it can be toxic to the environment. The traditional method used in the Chilean olive oil industry produces 20% oil and 80% wa...
Article
Full-text available
Abstract Cardiovascular disease (CVD) is the leading cause of death worldwide. Healthy eating is among its safeguards, especially the daily intake of fruits and vegetables. In this context it has been shown that tomato (Solanum lycopersicum) presents antiplatelet activity. In the present study, we evaluated in vitro antiplatelet activity of fresh h...
Article
Inhibition of acetylcholinesterase (AChE) is a common treatment for early stages of Alzheimer's disease. In this study, nine isoxazoles derivatives were tested for their in-vitro AChE activity. The molecular docking showed the interaction of the compounds with the active site. The isoxazoles were synthesized using 1,3-dipolar cycloaddition in the p...
Conference Paper
Due to the synthetic accessibility of different substituted coumarins and their biological properties, these heterocyclic compounds play an important role in the field of Medicinal Chemistry. In fact, coumarins have been previously described as anticancer, antiviral, anti-inflammatory, antimicrobial, enzymatic inhibitory and antioxidant agents. Wit...
Conference Paper
Full-text available
Quinoline is a heterocyclic scaffold of paramount importance to human race. Quinolines and their derivatives occur in numerous natural resources. Compounds containing quinoline structure are widely used as antiasthmatic, antimalarials, anti-viral, anti-inflammatory, antibacterials, antifungals, and anticancer (1). Among quinoline derivatives, tetra...
Conference Paper
Nitrogen heterocycles are a part of a special group of organic substances due to its many applications in the pharmaceutical market, exist a large number of structures carrying nitrogenous substances. Among these heterocycles the isoxazoles and tetrahydroquinolines (THQs)1 have shown significant biological activity on different therapeutic targets....
Conference Paper
Full-text available
Medicinal plants are organisms that are naturally endowed with chemical compounds (secondary metabolites) with properties of high therapeutic value, yielding advances in the development of synthetic drugs with physiological action beneficial to humans (ref). The use of these plants has an ancient origin in different cultures around the world and th...
Article
Full-text available
The tetrahydroquinoline ring system is a unit found in many biologically active natural products and pharmacologically relevant therapeutic agents. A new series of bistetrahydroquinolines (bis-THQs) was synthesized using imino Diels-Alder reactions between dialdehydes, anilines and N-vinyl-2-pyrrolidone (NVP). The notable features of this procedure...
Article
Abstract Nine synthetic isoxazoles were evaluated as antiplatelet agents and studied the possible mechanism of more active compound. The initial screening was evaluating all compounds against platelet aggregation assays. The most active compound was isoxazole 8 showing an inhibition of platelet aggregation around 70%. In subsequent experiments, ADP...
Article
Full-text available
In the past 30 years, only three natural products have been sources of new drugs with antiplatelet activity. In this study, we have demonstrated for the first time that guanosine from Solanum lycopersicum possesses antiplatelet (secretion, spreading, adhesion and aggregation) activity in vitro and inhibition of platelet inflammatory mediator of ath...
Article
Full-text available
The consumption of fruits and vegetables is accepted to be one of the strategies to reduce risk factors for these diseases. The aim of this study was to examine potential relationships between the antioxidant and the antiplatelet activities in green mature and fully ripe (red) tomatoes and of lycopene-rich byproducts of tomato paste processing such...
Article
In this study, we investigated the potential antibacterial, antioxidant and anti-platelet activities and the inhibition of cholinesterase from the methanolic extracts obtained from aerial parts of the two species of Azorella: A. spinosa (Constitution, Chile) and A. monantha (Torres del Paine, Enladrillado and Paso Vergara). All extracts showed only...