Adrián Ochoa-Terán

Adrián Ochoa-Terán
Tijuana Institute of Technology | ITT · Division of Graduate Studies and Research

Doctor in Sciences in Chemistry

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65
Publications
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655
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February 2004 - present
Tijuana Institute of Technology
Position
  • Researcher

Publications

Publications (65)
Article
In this work, a library of new aniline and pyridyl functionalized carbamoylcarboxylic acids were synthesized, physicochemically analyzed and evaluated as ligands for the simultaneous removal of environmental interest cations. The effect of the structural characteristics of these functionalized ligands over the simultaneous removal performance of me...
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The aminobenzamide–aminonaphthalimide fluorescent dyads allow the determination of Cu ²⁺ and Hg ²⁺ metal ion concentration from Förster Resonant Energy Transfer measurements.
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Nowadays, infectious diseases caused by drug-resistant bacteria have become especially important. Linezolid is an antibacterial drug active against clinically important Gram positive strains; however, resistance showed by these bacteria has been reported. Nanotechnology has improved a broad area of science, such as medicine, developing new drug del...
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Perezone is a naturally occurring hydroxyquinone that has been deeply studied from different chemical aspects, such as therapeutics, electrochemistry, physical–chemical properties, or synthetic approaches that turn it an attractive template for new semisynthetic derivatives with a wide range of purposes. Herein, we describe a facile synthetic pathw...
Article
In this work, nanoclusters (NCs) of Cu and Ag capped with hyperbranched polyethyleneimine (PEI) were prepared using chemical reduction by a one-step hydrothermal method. The PEI coated-NCs were characterized by high-resolution transmission electron microscopy, ζ potential, thermogravimetric analysis, dynamic light scattering, Fourier-transform infr...
Article
An efficient methodology for the synthesis of neutral reducing agents supported on Merrifield resin has been developed. The process was carried out under mild conditions, varying the linker length, the bidentate chelating amine and the alkali metal tetrahydroborate. Fluorescence and infrared spectroscopies and thermogravimetric analysis were used f...
Article
In this work, the interaction of three different pyridylalkyl mono-core substituted naphthalenedimides (NDIs) with metal ions was studied by UV-Vis and fluorescence spectroscopy. The influence of pyridine substituents position, the spacer length, and solvent over the metal ion recognition was investigated. The most sensible responses observed were...
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In this work new naphthalenediimides (NDIs) were synthesized and used as dyes in DSSC. The efficiency ( η ) of the DSSC is influenced by NDIs electronic and structural characteristics. It was found a better cell performance with the NDIs which have a broader absorption band shifted to the red color, high ƹ values, and more adsorption in the anode s...
Article
Both experimental and theoretical methods were used in order to study the fluorescent properties of nine new compounds based on phthalimides, isoindolin-1-ones and isoindolines bearing aminobenzoic acids (2-aminobenzoic acid, 3-aminobenzoic acid and 4-aminobenzoic acid), which were obtained under mild reaction conditions. The photophysical properti...
Article
The stereoselective synthesis and anti-Hymenolepis nana activity of six Linezolid-type compounds, obtained by chemical modification of L-Alanine, are reported in this work. The synthetic strategy was to prepare diastero-meric N,N-dibenzylamino oxazolidinones 1 and 2, and coupling with 4-(4-bromophenyl)morpholine (3) to obtain N,N-dibenzylamino Line...
Article
Nanogels are an important class of nanomaterials with a wide field of potential applications in nanomedicine. Fluorescent nanogels have the great advantage of the application in theranostics. In this study, intrinsic fluorescent nanogels, crosslinked with fluorescein O,O′-diacrylate (FDA), were synthetized and studied for first time, via a robust m...
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In this work, two types of MWCNT-oxazolidinone conjugates were synthesized, by varying the quartz tube lengths in the reactor (40 cm and 60 cm), with the aim at evaluating and comparing their biological potential against nine bacterial strains. MWCNT-1 (40 cm) showed higher surface defects and lower crystallinity than MWCNT-2 (60 cm). During each s...
Article
The quinazoline-2,4-diones scaffold is found in bioactive compounds, commercial drugs and exhibit important biological activities. However, their antidiabetic activity is rarely explored. For this purpose, an easy one-pot three-components and straightforward synthesis of 3-substituted quinazoline-2,4-diones was designed, in both, the catalyst- and...
Article
Two lignins extracted from coffee Arabica and stems of Typha domingensis (Tule) residues (CL and TL) are proposed as new multifunctional ecofriendly material for an effective removal of hazardous metal ions and organic matter contained in a typical metal finishing wastewater. The physicochemical characterization of CL and TL was achieve by FTIR, ¹H...
Article
Worldwide studies towards development of new drugs with a lower rate in emergence of bacterial resistance have been conducted. The molecular docking analysis gives a possibility to predict the activity of new compounds before to perform their synthesis. In this work, the molecular docking analysis of 64 Linezolid dipeptide-type analogues was perfor...
Article
s The recognition of histamine with copper and zinc complexes of polyazamacrocyclic ligans was studied. The molecular recognition of histamine from the metal complexes was determined by UV-Vis and ¹H NMR spectra in solution. In the coordination study of histamine with the Cu²⁺ complexes, different changes were observed in the charge transfer bands...
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A new series of oligomethylene bis(nitrophenylureylbenzamide) receptors were synthesized varying the relative position of the urea and amide groups (ortho 4 and meta 8) and the length of the oligomethylene chain (C2 to C8). An anion recognition study was performed with TBAX salts (X = AcO⁻, BzO⁻, F⁻, H2PO4⁻, and HP2O7³⁻) by UV-vis and ¹H NMR. The f...
Article
The synthesis of new alkyl (C3 to C8) bis(naphthylureylbenzamide)-based receptors and the study of their interaction with anions by UV–Vis, molecular fluorescence and ¹H NMR were performed. The results suggest both ureylbenzamide units participate in the complexion with anions due to their inherent flexibility, which promotes a cooperative binding...
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BACKGROUND: Worldwide, there has been an increase in type 2 diabetes mellitus (DM2) as a comorbidity of tuberculosis (TB), which is characterized by alterations in the pharmacokinetics of drugs used for TB treatment. OBJECTIVE : To characterize the pharmacokinetics of rifampin in patients with TB and TB-DM2. METHODS : Blood samples were collected i...
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Twelve new chiral chelating resins have been prepared using solid phase organic synthesis with the Merrifield and Wang resins and the bidentate amine 1,2‐ethylenediamine, followed by the coupling of asymmetric ketones such as 1‐phenyletanone, 4‐methyl‐2‐pentanone 4‐nitroacetophenone and 4‐methoxyacetophenone to form prochiral imines. The enantiosel...
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Two bis-urea type receptors were synthesized containing a polyether bridge and two 4-nitrophenyl groups as chromogenic units, R1 and R2. Molecular recognition studies of receptors towards different tetraalkylammonium and alkali metal salts were carried out in DMSO by UV-Vis and ¹H-NMR spectroscopy. The receptors were found to have high affinity for...
Article
A facile colorimetric method for rapid determination of Cr(III) ions was developed using 11-mercaptoundecylphosphonic acid modified gold nanoparticles (AuNPs-MPA) in aqueous medium. The reaction of AuNPs-MPA + Cr(III) ions were were characterized by FTIR and Uv-Vis spectroscopy. The presence of Cr(III) easily induced aggregation of AuNPs-MPA, resul...
Article
Herein we report an efficient synthesis of a series of non‐symmetrical naphthalenediimides (NDIs) bearing different neutral, electron‐donating and electron‐withdrawing groups in the imide moieties. The success of this method is based in the regioselective synthesis and isolation of pure carbamoyl naphthoic anhydride acid intermediates (CNA) in good...
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Physicochemical characterization (i.e., solubility, stability, UV–vis, IR, ¹H and ¹³C NMR, and thermogravimetric and elemental analysis) and biological activities (antioxidant and immunomodulatory) of purified melanins from the fruit flesh of Vitex mollis (VM) and Randia echinocarpa (RE) were investigated. The melanins showed low solubility, light...
Article
This paper proposes the use chitosan modified with carbamoyl benzoic acids as new coagulant-flocculant agents for metals removal from aqueous solutions. The grafted chitosan species as chitosan dianhydride (ChD) and chitosan dianhydride-amine (ChDA) improved the removal of Cu2+, Pb2+, Ca2+, Cr3+, Zn2+ and Ni2+, compared with chitosan alone. Zeta po...
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A new group of ureylbenzamide-based receptors (1–4) has been synthesized; its binding affinity and capacity to form supramolecular complexes in solution with different anions have been investigated. For designing these receptors, it was considered a combination of the positions of the urea and amide groups (ortho and meta), and the chromophore grou...
Article
In this work, the optical properties of N,N-bis(aminobenzyl)naphthalenediimides 2a–2d (BzNDIs) and their interaction with fluoride were studied. The results demonstrated that the amino group position in the benzyl substituent exerts an effect in the absorption and emission properties. Particularly, the N,N-bis(2-aminobenzyl)NDI 2b presented non-typ...
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1,2,3-Benzotriazinones were synthesized in excellent yields by the reaction of 2-( o -aminophenyl)oxazolines and isoamyl nitrite in methanol. The crystal structure of the acetyl derivative of one of the 1,2,3-benzotriazinones provided additional support for the spectroscopic structural characterization of the title compounds.
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In this manuscript is described a research related with two ditopic receptors based on 4,4′-carbonyl bis(carbamoylbenzoic) acids bearing a naphthyl (2a) and naphthylmethyl fluorophores (2b), which interact with metal ions. The fluorescence properties of both receptors were influenced by the connectivity with the amide group. The non-spaced receptor...
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The quinazolin-2,4-dione moiety is found in many compounds with important biological activities making it a target for its synthesis. In this work, a one-pot three-step synthesis of new quinazolin-2,4-diones from phthalic anhydrides and their activity against Leishmania mexicana are described. The new quinazolin-2,4-diones were isolated with yields...
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Benzoxazinediones exhibit potential as versatile synthons in the synthesis of wide variety of heterocyclic compounds with biological activity. In this work, an efficient and eco-friendly onestep synthesis of benzoxazine-2,4-diones from phthalic anhydrides derivatives and trimethylsilyl azide using the microwave technique was developed and compared...
Article
The use of carbamoyl benzoic, acids as separation new agents, to remove on the hazardous heavy metals, that are frequently, contained in metal plating wastewater is reported in this paper. The interaction of ionic heavy metals and carbamoyl benzoic acids was studied approaching zeta potential in aqueous solutions. These carbamoyl acids are innovati...
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Silver nanoparticles coated with molecularly imprinted silica shell (Ag@SiO2-MIP) were synthesized, and their properties for the molecular recognition and the controlled delivery of tetracycline (TC) in aqueous environments were investigated. In this study, a synthesis protocol based in the entrapping of TC into silica particles with a core of silv...
Article
The change in fluorescent properties of a series of N,N-bis(pyridylmethyl)naphthalenediimides (BIPy-NDIs) as function of pH were investigated. The naphthalenediimide dyes displayed OFF–ON pH sensing properties owing to photoinduced electron transfer in the pH range from 1.7 to 4.1. The fluorescence enhancement of the chemosensors studied is based o...
Article
A series of novel naphthalimide–aminobenzamide (NAPIM-2ABZ) dyads 3 connected by different length polymethylene chains were synthesized and studied as fluorescent supramolecular receptors in metal ion binding. The photophysical properties were evaluated and compared with separated chromophores. The electronic absorption spectra of dyads 3 showed no...
Article
A new 1, 4, 5, 8-naphthalene diimide functionalized with two 3-phenylboronic acid groups (1) was prepared and employed as a selective sensor for fluoride. The proposed sensor is based on anion-π interactions between fluoride and naphthalene diimide core and the cooperative effect of boronic acid groups acting as Lewis acid anion receptors. The resu...
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Treatment of phthalic anhydride derivatives with trimethylsilyl azide affords benzimidazolin-2-ones in 45–91% yield, which is the result of two consecutive Curtius reactions. Within the series obtained, 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one showed highest antioxidant activity.
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The efforts for synthesis of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters 6 are reported in good yields from an in situ generated α-azidomethyl ketone. Optimum experimental conditions were established for preparation of α-halomethyl ketones 10 and α-N,N-dipropargylamino esters 11, all derived from α-amino acids. The starting materi...
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A simple and efficient microwave-assisted methodology for the synthesis of 4-substituted-3-methyl-1,3-oxazolidin-2-ones from amino alcohols catalyzed by a ionic liquid was developed. This novel one-pot and one-step cyclization-methylation reaction represents an easier and faster method than any other reported protocols that can be used to obtain th...
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Efficiency of coagulation-flocculation process used for semiconductor wastewater treatment was improved by selecting suitable conditions (pH, polyelectrolyte type, and concentration) through zeta potential measurements. Under this scenario the zeta potential, 𝜁, is the right parameter that allows studying and predicting the interactions at the mole...
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Staphylococcus aureus is one of the most common causes of nosocomial infections. The purpose of this study was the synthesis and in vitro evaluation of antimicrobial activity of 10 new 3-oxazolidin-2-one analogues on 12 methicillin resistant S. aureus (MRSA) clinical isolates. S. aureus confirmation was achieved via catalase and coagulase test. Mol...
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A regioselective synthesis has been developed for the preparation of a series of N,N'-disubstituted 4,4'-carbonylbis(carbamoylbenzoic) acids and N,N'-disubstituted bis(carbamoyl) terephthalic acids by treatment of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (1) and 1,2,4,5-benzenetetracarboxylic dianhydride (2) with arylalkyl primary amines (...
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A facile one-step synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides and TMSA was described. This paper determines their antimicrobial activity against nine human bacterial pathogens by the broth microdilution method; antioxidant activity by DPPH • inactivation and a ferric-reducing power assay; and toxicity by a brine shrimp, Arte...
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This paper describes a novel dual emission bis-1,8-naphthalimide sensor for selective determination of pH and Pb2+ ions. The influence of the variability in the backbone that links the two fluorophores (naphthalimides) as a function of pH and metal ions was studied by UV-visible and fluorescence spectroscopy. Compounds 1(a-d) with different length...
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In this paper is describing the physicochemical behavior of polyelectrolytes (PEs) used in waste water treatment with mono-, di- and trivalent metal ions as K+, Mg2+, Zn2+, Fe3+, Sn2+, Cd2+, Pb2+, Cu2+, Ni2+, Al3+ and Cr3+. A coagulant polyelectrolyte Poly(vinyl sulfate) potassium salt (PVSK), and a commercial available Flocculant Trident 2756, wer...
Article
In this paper, we report the synthesis of morin covalently attached to Merrifield’s resin to be used in metal sorption and recognition. The potential in sensing and sorbent properties of these materials for Cu(II), Pb(II), Zn(II) and Cd(II) in batch and using a flow-through optosensing approach is outlined. The sorption capacity was evaluated in a...
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In this paper the synthesis of a library of new 1,4-disubstituted 1,2,3-triazoles 1, with a variety of additional functional groups on its structure, from an in situ generated benzyl azide 2 and different alkynes and dialkynes 3 is reported. Optimal experimental conditions were established for the conventional click chemistry and for the microwave-...
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Cycloalkanespirohydantoins 3 and piperidinespirohydantoins 4 were synthesized from cycloalkanones 9 and piperidones 10 under microwave-assisted conditions. Results are compared with those obtained under thermal conditions. Cycloalkanespirohydantoins 3 were N-protected with Boc group and hydrolyzed under basic conditions to obtain five, six and seve...
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A new method to obtain enantiopure trisubstituted piperidines 1 by reaction of chiral epoxyaziridine 2 with α-amino esters 3 in the presence of a Lewis acid is reported. This synthesis took place through the successive opening of both oxirane and aziridine rings of 2 by the amino group of the corresponding α-amino ester 3 with total chemo-and regio...
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In this paper, we report the synthesis on Merrifield's resin of alkyl-bis-o-aminobenzamides labeled with a fluorescent dansyl group for use in metal ion recognition. The influence of alkyl groups with different long chains (n = 1, 2, 4, 6) on the spectral fluorescence characteristics was studied. The sensing properties of the beads were evaluated b...
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A new method to obtain enantiopure 5-substituted 1,3-oxazolidin-2-ones 1 from α-dibenzylamino esters 2 is reported. This methodology is based on the Lewis acid catalyzed stereoselective addition of trimethylsilyl cyanide to chiral α-dibenzylamino aldehydes 3. Magnesium chloride and zinc iodide were tested to catalyze the addition, obtaining higher...
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Mephenoxalone (1) was synthesized through a silanizated intermediate prepared from the addition of trimethylsilyl cyanide (TMSCN) to (o-methoxy)phenoxyacetaldehyde (10). Three different methods were established to synthesize this aldehyde. Alkylation of guaiacol with bromoacetaldehyde diethyl acetal, followed by acid hydrolysis of acetal group gave...
Article
The preparation of a 12-membered ring macrolactone model of auriside that contains a pendant diene chain bearing a bromide was investigated employing two approaches. The first approach utilized an oxidative rearrangement of a tertiary allylic alcohol on a 12-membered ring. The second approach was based on a 1,4-methylation of an ynone followed by m...
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Chiral aminoalkyl epoxyaziridine 1 is synthesized in high yield and diastereoselectivity from L-serine. Ring opening of epoxyaziridine 1 with primary amines is carried out with total chemo- and regioselectivity, affording chiral polyfunctionalized piperidines 8. The structure of these trisubstituted piperidines is established by NMR studies.
Article
A Vilsmeier salt supported on solid phase was prepared using piperazine bound to Merrifield resin. Piperazine was selected because it contains two secondary amines: one of the amines is protected upon binding to the resin, and the second was formylated to give resin-1-N-piperazine-4-N-carboxaldehyde (9). Activation of the formamide with either bis(...
Article
A new approach on the use of mass spectrometry direct-insertion and a quadrupole detector for analysis of organic compounds supported in solid phase has been developed. This is a simple and efficient method based on cleavage due to the thermal-instability of the benzylic group of most commercial resins. The cleavage of supported compounds takes pla...
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Alkyl esters of several amino acids and acids were prepared using triphosgene [t richloromethyl carbonate, TPA (2)].
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Addition of trimethylsilyl cyanide (TMSCN) to aldehydes was catalyzed by Montmorillonite-K10, with subsequent reduction to beta-aminoalcohol. In recent years we have explored a number of methodologies for the preparation of beta-aminoalcohols(1-4), many of which are biologically active and are also versatile intermediates in organic synthesis as hi...

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