Papers by Erick Cuevas-Yañez
Tetrahedron, 2004, 60, 1505-1511, 2004
a-Diazo-b-ketoesters and a-diazoketones derived from 2-pyrrolylacetic, 2-pyrrolylpropionic, 3-ind... more a-Diazo-b-ketoesters and a-diazoketones derived from 2-pyrrolylacetic, 2-pyrrolylpropionic, 3-indolylacetic and 3-indolylpropionic acids afforded carbenoid derived cyclization products on treatment with catalytic rhodium(II) acetate.
Journal of Nanomaterials, 2017
Cancer is one of the diseases with most deaths worldwide, around 8.2 million annually. For this r... more Cancer is one of the diseases with most deaths worldwide, around 8.2 million annually. For this reason, several treatments and diagnostic tools have been investigated and developed over the past decades. Among them, a dual-image system has been developed to achieve and enhance the detection of cancer, which has not been done with systems currently available. The present study describes the preparation of a dual-image targeting system composed of magnetic iron oxide nanoparticles functionalized with folic acid and rhodamine; nanoparticles synthesis was achieved by a coprecipitation method; the functionalization was carried out by a carbodiimide with folic acid and/or the rhodamine isothiocyanate; conjugates were characterized by spectrometric techniques; toxicity was measured by cell proliferation assay on HeLa cells using progressive concentrations of functionalized nanoparticles. Cellular uptake assay was carried out by competitive assay on HeLa cells. Iron oxide magnetite nanopart...
Organic Letters, 2007
Phosphorus dendrimer immobilized azabis(oxazoline) ligands can be efficiently synthesized up to t... more Phosphorus dendrimer immobilized azabis(oxazoline) ligands can be efficiently synthesized up to the third generation with 48 ligand molecules being attached to the periphery using click chemistry. The so-assembled macromolecules were evaluated in copper(II)-catalyzed asymmetric benzoylations, showing good yields and enantioselectivities. Moreover, the copper(II)-catalysts could be readily recovered and reused in several cycles. The globular structure of the dendritic ligands seems to prevent interference of the triazole moieties in the catalysis, contrasting MeOPEG or polystyrene bound ligands of the same type.
Tetrahedron …, 2001
... Corresponding author. Tel.: (52) 56 22 44 28; fax: (52) 56 16 22 17; e-mail: raymundo@ servid... more ... Corresponding author. Tel.: (52) 56 22 44 28; fax: (52) 56 16 22 17; e-mail: raymundo@ servidor.unam.mx ... After 2 h of stirring the reaction mixture was quenched by drop-wise addition of water, extracted with EtOAc and washed with water and brine. ...
Tetrahedron: Asymmetry, 2017
Abstract Two novel chiral structurally azabis(oxazoline) ligands were synthesized using (+)-camph... more Abstract Two novel chiral structurally azabis(oxazoline) ligands were synthesized using (+)-camphor as the starting material. Each of the ligands was prepared through the corresponding aminoalcohols. The structures of some crystalline derivatives were unambiguously established by X-ray analysis.
The synthesis of 2-diazo-1-(2-(thiophen-2-ylmethoxy)- phenyl)-ethanone (1) is described. The proc... more The synthesis of 2-diazo-1-(2-(thiophen-2-ylmethoxy)- phenyl)-ethanone (1) is described. The procedure involves an aromat- ic nucleophilic substitution between the sodium 2-thiophenyl methoxide and 2-fluorobenzaldehyde, the subsequent mild-condition oxidation to the corresponding carboxylic acid, and final transforma- tion through carbonic-carboxylic anhydride intermediate to the a-dia- zoketone. Treatment of compound 1 with catalytic amounts of rhodi- um (II) acetate gives the thienylmethyl benzofuranone 10 which comes from the (2,3) sigmatropic rearrangement of the oxonium ylide 9 derived from the rhodium carbenoid that is postulated as reaction
Medicinal Chemistry Research, 2019
A novel series of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives was synthesized from 1-ary... more A novel series of 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives was synthesized from 1-aryl-1,3-diazidopropan-2-ol derivatives and diverse alkynes using copper catalyzed azide-alkyne cycloaddition in the key step. Most of synthesized compounds showed high activity against Candida spp. strains at a 0.04–0.5 μg/mL concentration range compared to Itraconazole and Fluconazole (MIC 2.56 and 1.28 μg/mL, respectively), which were used as reference compounds. A 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivative (R1 = F and R2 = cyclopropyl) displayed an outstanding selectivity against Candida albicans and Candida krusei (MIC = 0.0075 µg/mL). Moreover, Artemia salina bioassay on 1,3-bis-(1,2,3-triazol-1-yl)-propan-2-ol derivatives revealed low toxicity in this kind of compounds. In addition, molecular docking studies suggest good binding affinity of halogen atoms in some 1-aryl-1,3-diazidopropan-2-ol derivatives to HEME group present in 14-alpha demethylase (CYP51), which might expla...
Resumen. Se describe la síntesis de la 2-diazo-1-[2-(2-tiofenilmetoxi)-fenil]-etanona (1) la cual... more Resumen. Se describe la síntesis de la 2-diazo-1-[2-(2-tiofenilmetoxi)-fenil]-etanona (1) la cual involucra la reacción de sustitución nucleofílica aromática del (2-tiofenil) metóxido de sodio con 2-flurorobenzaldehído, la oxidación en condiciones suaves del grupo aldehído al ácido carboxílico y posteriormente la transformación a α-diazocetona a través de un anhídrido carbónico-carboxílico como intermediario de reacción. El tratamiento del compuesto 1 con cantidades catalíticas de acetato de rodio (II) da la tiofenilmetil benzofuranona 10 por medio de una transposición sigmatrópica [2,3] del iluro de oxonio 9 derivado del carbenoide de rodio que se postula como intermediario de reacción. Palabras clave: α-diazocetona, ciclización, carbenoide de rodio.
Journal of Chemical Sciences, 2019
A small library of diverse 1,1-diaryl-2-(1,2,3)triazol-1-yl-ethanol derivatives was designed and ... more A small library of diverse 1,1-diaryl-2-(1,2,3)triazol-1-yl-ethanol derivatives was designed and prepared from CuAAC reaction as the key step. The molecular structure of some representative compounds was unambiguously determined from X-ray diffraction studies. In addition, synthesized 1,2,3-triazoles were evaluated for activity against filamentous fungi (Mucor hiemalis, Aspergillus fumigatus, Trichosporon cutaneum, and Rhizopus oryzae) and yeasts that belong to the genus Candida. Two compounds showed high activity against C. utilis (MIC 0.5 $$\upmu \mathrm{{g/mL}}$$μg/mL) and A. fumigatus (MIC 4 $$\upmu \mathrm{{g/mL}}$$μg/mL) which is close to itraconazole used as reference compound.Graphical Abstract1,1-diaryl-2-(1,2,3)triazol-1-yl-ethanol analogues to flutriafol were prepared from CuAAC reaction and the molecular structure of some representative compounds was unambiguously determined from X-ray diffraction studies. Some of these 1,2,3-triazoles displayed activity against filament...
Current medicinal chemistry, 2021
An important group of anti-emetic drugs used in the treatment of nausea and vomiting after chemot... more An important group of anti-emetic drugs used in the treatment of nausea and vomiting after chemotherapy contains an indole moiety in their structures, working as 5-hydroxytryptamine type 3 serotonin receptor antagonist (5-HT3). This revision is focused on compounds bearing an indole core that present a 5-HT3 receptor antagonist activity that has been successfully used as anti-emetic drugs, reducing chemotherapy adverse secondary effects during cancer treatment. Their synthesis, biological activities, and some outstanding characteristics are discussed, affording a general outlook towards the development of more efficient anti-emetic drugs.
The synthesis of new unsymmetrical A3B porphyrin, 5,10,15-tri(4-methoxyphenyl)-20-(4-chlorophenty... more The synthesis of new unsymmetrical A3B porphyrin, 5,10,15-tri(4-methoxyphenyl)-20-(4-chlorophentyl)-21H,23H-porphyrin, 1, and its zinc(II) complex, 5,10,15-tri(4-methoxyphenyl)-20-(4-chlorophentyl)-21,23-Zinc(II)-porphine, 2, was accomplished using both conventional and "one pot" solventless microwave assisted methods with interesting comparative results. The obtained molecules were characterized by H NMR, UV-Vis and MS. These molecules are considered to represent new compounds with potential application as photosensitizers in photodynamic therapy.
The syntbesis of new unsymmetrical A,B porphyrin. 5,lO,15-tri(4-methoxypheoy1)-20-(4-chloropheoy1... more The syntbesis of new unsymmetrical A,B porphyrin. 5,lO,15-tri(4-methoxypheoy1)-20-(4-chloropheoy1)-21H, 23H-porphyrin. 1. and its Zinc(ll) comp1ex, 5,1 O,15-tri( 4-methoxypheoy1)-20-( 4-ch1oropheoy1)-21, 23- Zinc(II)-pmphine, 2, was accomplished using botb conveotional and "one pot' solventless microwave assisted methods with interesting comparative results. The obtained molecules were characterized by H NMR, UV-Vis and MS. These molecules are considered to represent new compounds with potential application as pbotosensitizers in photodynamic thempy.
Keratin, obtained from chicken feathers, was grafted on the surface of commercially available car... more Keratin, obtained from chicken feathers, was grafted on the surface of commercially available carbon nanotubes. The original procedure developed allows a covalent interaction between some specific chemical groups characteristic of the keratin, with some functional groups introduced on purpose on the surface of the nanotubes, as revealed by infrared and Raman spectroscopies, which also allowed to determine structural changes introduced during the process, such as crystallinity, which lead to changes in other properties, as well.
The click chemistry was employed on oxidized multiwall carbon nanotubes for their functionalizati... more The click chemistry was employed on oxidized multiwall carbon nanotubes for their functionalization with 1,3-diazido-2-isopropanol (2N3OH). Phenylacetylene and propargylamine are used as alkyne groups, catalyzed with copper iodide (I). The chemical and structural characterization are described starting from the Raman and infrared spectroscopy as well as the realization of an elemental combustion analysis, transmission electron microscopy and nuclear magnetic resonance (NMR).
1,2,3-Triazoles were synthesized from a variety of alkyne and azides using silver compounds. Addi... more 1,2,3-Triazoles were synthesized from a variety of alkyne and azides using silver compounds. Additionally to common silver salts (nitrate, sulphate, oxide and chloride), we also tried an Nheterocyclic “abnormal” complex, a derivative of a mesoionic carbene, that proved to be a better catalytic system. Good yields of the 1,2,3-triazoles were obtained, by means of an alternative methodology, avoiding side reactions, the use of additives and facilitating the purification of final products. A plausible mechanism were proposed, according to the literature.
A small library of 1,2,3-triazoles was synthesized from diverse alkynes and azides using catalyti... more A small library of 1,2,3-triazoles was synthesized from diverse alkynes and azides using catalytic amounts of an alkynylcopper (I) complex, which in turn was prepared from direct treatment of phenylacetylene with a Fehling reagent in the presence of glucose as a reducing agent. The results suggest that copper-catalyzed azide alkyne cycloaddition (CuAAC) reactions require only 0.5 mg/mmol copper (I) phenylacetylide without any further additives.
Comprehensive Heterocyclic Chemistry IV
Abstract This article covers an overview of synthesis and reactivity of azoniaspiro compounds. Th... more Abstract This article covers an overview of synthesis and reactivity of azoniaspiro compounds. The spirocyclic ammonium derivatives contain a nitrogen atom at the point of fusion. These quaternary compounds are isolated and characterized as salts. A brief update on experimental and structural methods of azoniaspiro salts is given. Theoretical concepts and thermodynamic aspects are illustrated. The synthesis of all types of azoniaspiro derivatives is described, which includes recent examples of different ring formation. Finally, the importance of these compounds and their broad spectrum of applications are presented.
Chemistry Proceedings
An array of 2,4-disubstituted thiazolines was obtained through Asinger reaction approach from the... more An array of 2,4-disubstituted thiazolines was obtained through Asinger reaction approach from the straightforward treatment of diverse aldehydes/ketones with 1-mercaptopropan-2-one, in the presence of NH3 assisted by microwave irradiation, displaying similar and sometimes higher yields, as well as shorter reaction times that traditional Asinger reaction conditions at room and lower temperatures.
Tetrahedron
Abstract The purpose of this review is to discuss 1) how free radical chemistry has contributed t... more Abstract The purpose of this review is to discuss 1) how free radical chemistry has contributed to development of new methodologies for the construction of 10-membered and larger macrocycles over the past 32 years; 2) the most well-developed free radical methods for constructing 10-membered and larger rings; and 3) how these methodologies have contributed to solving certain key steps in the synthesis of natural products.
Uploads
Papers by Erick Cuevas-Yañez