30 results on '"Daniel Canseco-González"'
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2. Relevance of Fluorinated Ligands to the Design of Metallodrugs for Their Potential Use in Cancer Treatment
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José C. Páez-Franco, Miriam R. Zermeño-Ortega, Carmen Myriam de la O-Contreras, Daniel Canseco-González, Jesus R. Parra-Unda, Alcives Avila-Sorrosa, Raúl G. Enríquez, Juan M. Germán-Acacio, and David Morales-Morales
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organometallics ,coordination complexes ,metallodrugs ,fluorinated ligands ,anticancer activity ,cancer ,Pharmacy and materia medica ,RS1-441 - Abstract
Fluorination of pharmaceutical agents has afforded crucial modifications to their pharmacological profiles, leading to important advances in medicinal chemistry. On the other hand, metallodrugs are considered to be valuable candidates in the treatment of several diseases, albeit with the caveat that they may exhibit pharmacological disadvantages, such as poor water solubility, low bioavailability and short circulating time. To surmount these limitations, two approaches have been developed: one based on the design of novel metallodrug-delivering carriers and the other based on optimizing the structure of the ligands bound to the metal center. In this context, fluorination of the ligands may bring beneficial changes (physicochemical and biological) that can help to elude the aforementioned drawbacks. Thus, in this review, we discuss the use of fluorinated ligands in the design of metallodrugs that may exhibit potential anticancer activity.
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- 2022
- Full Text
- View/download PDF
3. Synthesis of New bis-furanyl-pyrrolo[3,4-b]pyridin-5-ones via the Ugi-Zhu Reaction and Docking Studies on the Main Protease (MPro) from SARS-CoV-2
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Ivette Morales-Salazar, Sandra L. Castañón-Alonso, Daniel Canseco-González, Erik Díaz-Cervantes, Eduardo González-Zamora, and Alejandro Islas-Jácome
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Ugi-Zhu reaction ,polyheterocycles ,docking ,COVID-19 ,SARS-CoV-2 ,main protease MPro ,Chemistry ,QD1-999 - Abstract
The synthesis of five new bis-furanyl-pyrrolo[3,4-b]pyridin-5-ones in 30 to 40% yields through a domino sequence based on the Ugi-Zhu three-component reaction is described. Then, on the main protease MPro (PDB: 6lu7) from the SARS-CoV-2, the synthesized products and co-crystallized ligands of MPro were in silico evaluated using the docking technique, finding moderate to good binding energies and some interesting interactions, demonstrating that the ligand 8c can be considered as a drug candidate against the SARS-CoV-2-MPro due to its LE value (−5.96 kcal/mol), which is better than other synthesized and reported molecules in the literature. At the same time, hydrophobic interactions play a crucial role in the ligand target molecular couplings, demonstrated through a hydrophobicity surfaces analysis. Finally, 8a and 8b can also be considered as drug candidates. Thus, some synthesized bis-furanyl-pyrrolo[3,4-b]pyridin-5-ones may be used for further in vitro assays against the virus.
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- 2021
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4. Synthesis, Characterization, and Intrinsic Dissolution Studies of Drug–Drug Eutectic Solid Forms of Metformin Hydrochloride and Thiazide Diuretics
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Guadalupe Coyote-Dotor, José C. Páez-Franco, Daniel Canseco-González, Alejandra Núñez-Pineda, Alejandro Dorazco-González, Inés Fuentes-Noriega, Alfredo R. Vilchis-Néstor, Joelis Rodríguez-Hernández, David Morales-Morales, and Juan Manuel Germán-Acacio
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drug–drug eutectic solid forms ,mechanochemical reactions ,intrinsic dissolution experiments ,Pharmacy and materia medica ,RS1-441 - Abstract
The mechanochemical synthesis of drug–drug solid forms containing metformin hydrochloride (MET·HCl) and thiazide diuretics hydrochlorothiazide (HTZ) or chlorothiazide (CTZ) is reported. Characterization of these new systems indicates formation of binary eutectic conglomerates, i.e., drug–drug eutectic solids (DDESs). Further analysis by construction of binary diagrams (DSC screening) exhibited the characteristic V-shaped form indicating formation of DDESs in both cases. These new DDESs were further characterized by different techniques, including thermal analysis (DSC), solid state NMR spectroscopy (SSNMR), powder X-ray diffraction (PXRD) and scanning electron microscopy–energy dispersive X-ray spectroscopy analysis (SEM–EDS). In addition, intrinsic dissolution rate experiments and solubility assays were performed. In the case of MET·HCl-HTZ (χMET·HCl = 0.66), we observed a slight enhancement in the dissolution properties compared with pure HTZ (1.21-fold). The same analysis for the solid forms of MET·HCl-CTZ (χMET·HCl = 0.33 and 0.5) showed an enhancement in the dissolved amount of CTZ accompanied by a slight improvement in solubility. From these dissolution profiles and saturation solubility studies and by comparing the thermodynamic parameters (ΔHfus and ΔSfus) of the pure drugs with these new solid forms, it can be observed that there was a limited modification in these properties, not modifying the free energy of the solution (ΔG) and thus not allowing an improvement in the dissolution and solubility properties of these solid forms.
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- 2021
- Full Text
- View/download PDF
5. Mechanochemistry: A Green Approach in the Preparation of Pharmaceutical Cocrystals
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Mizraín Solares-Briones, Guadalupe Coyote-Dotor, José C. Páez-Franco, Miriam R. Zermeño-Ortega, Carmen Myriam de la O Contreras, Daniel Canseco-González, Alcives Avila-Sorrosa, David Morales-Morales, and Juan M. Germán-Acacio
- Subjects
mechanochemistry ,green reactions ,pharmaceutical cocrystals ,Pharmacy and materia medica ,RS1-441 - Abstract
Mechanochemistry is considered an alternative attractive greener approach to prepare diverse molecular compounds and has become an important synthetic tool in different fields (e.g., physics, chemistry, and material science) since is considered an ecofriendly procedure that can be carried out under solvent free conditions or in the presence of minimal quantities of solvent (catalytic amounts). Being able to substitute, in many cases, classical solution reactions often requiring significant amounts of solvents. These sustainable methods have had an enormous impact on a great variety of chemistry fields, including catalysis, organic synthesis, metal complexes formation, preparation of multicomponent pharmaceutical solid forms, etc. In this sense, we are interested in highlighting the advantages of mechanochemical methods on the obtaining of pharmaceutical cocrystals. Hence, in this review, we describe and discuss the relevance of mechanochemical procedures in the formation of multicomponent solid forms focusing on pharmaceutical cocrystals. Additionally, at the end of this paper, we collect a chronological survey of the most representative scientific papers reporting the mechanochemical synthesis of cocrystals.
- Published
- 2021
- Full Text
- View/download PDF
6. Crystal structure of 1-mesityl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium iodide
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Daniel Canseco-González, Juventino J. García, and Marcos Flores-Alamo
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crystal structure ,triazolium salt ,mesityl group ,C—H...I hydrogen bonds ,Crystallography ,QD901-999 - Abstract
In the cation of the title salt, C18H20N3+·I−, the mesityl and phenyl rings are inclined to the central triazolium ring by 61.39 (16) and 30.99 (16)°, respectively, and to one another by 37.75 (15)°. In the crystal, molecules are linked via C—H...I hydrogen bonds, forming slabs parallel to the ab plane. Within the slabs there are weak π–π interactions present involving the mesityl and phenyl rings [inter-centroid distances are 3.8663 (18) and 3.8141 (18) Å].
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- 2015
- Full Text
- View/download PDF
7. Front Cover: Facile, Single‐Step Synthesis of a Series of D‐Ring Ethisterones Substituted with 1,4‐1,2,3‐Triazoles: Preliminary Evaluation of Cytotoxic Activities (ChemMedChem 8/2023)
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Daniel Canseco‐González, Isaac Rodríguez‐Victoria, Teresa Apan‐Ramírez, Alejandro O. Viviano‐Posadas, Juan S. Serrano‐García, Antonino Arenaza‐Corona, Adrian L. Orjuela, Jorge Alí‐Torres, Alejandro Dorazco‐González, and David Morales‐Morales
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Pharmacology ,Organic Chemistry ,Drug Discovery ,Molecular Medicine ,General Pharmacology, Toxicology and Pharmaceutics ,Biochemistry - Published
- 2023
8. Facile, Single‐Step Synthesis of a Series of D‐Ring Ethisterones Substituted with 1,4‐1,2,3‐Triazoles: Preliminary Evaluation of Cytotoxic Activities
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Daniel Canseco‐González, Isaac Rodríguez‐Victoria, Teresa Apan‐Ramírez, Alejandro O. Viviano‐Posadas, Juan S. Serrano‐García, Antonino Arenaza‐Corona, Adrian L. Orjuela, Jorge Alí‐Torres, Alejandro Dorazco‐González, and David Morales‐Morales
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Pharmacology ,Organic Chemistry ,Drug Discovery ,Molecular Medicine ,General Pharmacology, Toxicology and Pharmaceutics ,Biochemistry - Published
- 2023
9. Identification of anthocyanic profile and determination of antioxidant activity of Dahlia pinnata petals: A potential source of anthocyanins
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Sulem Yali Granados‐Balbuena, Ericka Santacruz‐Juárez, Daniel Canseco‐González, Lucía Aztatzi‐Rugerio, Lilia Sánchez‐Minutti, Carolina Ramírez‐López, and Erik Ocaranza‐Sánchez
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Anthocyanins ,Tandem Mass Spectrometry ,Dahlia ,Flowers ,Antioxidants ,Chromatography, Liquid ,Food Science - Abstract
In recent decades, the food industry has focused on the search for potential sources of anthocyanins that are able to provide color to replace synthetic dyes and at the same time provide health benefits through food products. Thus, in the present work, we propose the Dahlia pinnata flower as a potential source of anthocyanins. The dahlia is a native, annual flower from Mexico with a wide diversity of shapes and colors. The ancestral use of the flower in several dishes, its abundance, and the intense color of the flowers known as black make the D. pinnata flower a suitable candidate to be considered as a potential source of anthocyanins. Thus, the aim of this research is the determination of its nutritional composition, anthocyanin profile, and antioxidant activity. For this purpose, proximate composition of petals was determined by the AOAC standard methods. Anthocyanins were extracted from the dried petals of the flower with 0.1% HCl in methanol and 70% aqueous acetone solution and purified through Amberlite-XAD7-HP resin. Then, the purified extracts were analyzed for antioxidant activity by the DPPH method and the anthocyanin profile was characterized by HPLC and UPLC-MS/MS. Results showed that D. pinnata flowers have a proximate composition similar to other important edible flowers with a high level of moisture (87%-92%) and fiber (6%-7%). The antioxidant activity of both purified extracts was considerable (2.6-12 g/ml) compared to other sources of anthocyanins. The anthocyanin profile of the purified extracts contains four main anthocyanins: delphinidin-3-glucoside, delphinidin-3-rutinoside, pelargonidin-3-sambubioside-5-glucoside, and peonidin-3-sambubioside-5-glucoside, the last two being uncommon as major anthocyanin components in other plant sources. PRACTICAL APPLICATION: We present a potential and novel source of anthocyanins based on anthocyanin content and antioxidant activity of Dahlia pinnata petals. On the basis of UPLC-MS/MS studies, we identified four main anthocyanins, so this information provides the opportunity to study the source in many areas such as natural pigment stabilization, food additives, and antioxidants.
- Published
- 2022
10. Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case
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Daniel Canseco-González, José Luis Rodríguez de la O, and José Enrique Herbert-Pucheta
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010405 organic chemistry ,Chemistry ,chemistry.chemical_element ,Organic chemistry ,010402 general chemistry ,01 natural sciences ,Copper ,Cycloaddition ,0104 chemical sciences ,Paramagnetism ,13c nmr spectroscopy ,QD241-441 ,Polymer chemistry ,Click chemistry - Abstract
Copper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) click chemistry robustness has been demonstrated over recent years to produce 1,2,3-triazoles with excellent yields at mild conditions with simple purification methods. However, the consequences of having copper paramagnetic traces in final products, which complicate spectroscopic assignments and can produce inaccurate conclusions, has been scarcely discussed. Herein we present a strategy that combines X-Ray Diffraction (XRD) with 13C- paramagnetic Nuclear Magnetic Resonance spectroscopy, in order to demonstrate the presence of paramagnetic metal traces at standard Huisgen synthesis and purification conditions. We also demonstrate that the derivatization of 1,4-disubstituted-1,2,3-triazoles to produce 1,3,4,-trisubstituted-1,2,3.triazolium salts, promotes an efficient removal of Cu(II/I) moieties. Evidence of paramagnetic metal moieties is given using XRD structural analysis of abnormalities in torsional angles between substituents and the 1,2,3-triazole center, in parallel to 13C- paramagnetic NMR chemical shift and line width analysis. As model systems to demonstrate the importance of characterizing paramagnetic traces, we present the synthesis of novel 1-((3s,5s,7s)-adamantan-1-yl)-4-cyclopropyl-1H-1,2,3-triazole and its derivatized 1-((3s,5s,7s)-adamantan-1-yl)-4-cyclopropyl-3-methyl-1H-[1,2,3]-triazol-3-ium triflate salt.
- Published
- 2019
11. Synthesis, Characterization, and Intrinsic Dissolution Studies of Drug–Drug Eutectic Solid Forms of Metformin Hydrochloride and Thiazide Diuretics
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Daniel Canseco-González, Inés Fuentes-Noriega, David Morales-Morales, José C. Páez-Franco, Joelis Rodríguez-Hernández, Alejandra Núñez-Pineda, Juan Manuel Germán-Acacio, Alfredo R. Vilchis-Nestor, Alejandro Dorazco-González, and Guadalupe Coyote-Dotor
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Scanning electron microscope ,Chemistry ,Pharmaceutical Science ,Article ,RS1-441 ,intrinsic dissolution experiments ,Pharmacy and materia medica ,Solid-state nuclear magnetic resonance ,drug–drug eutectic solid forms ,medicine ,Solubility ,Thermal analysis ,mechanochemical reactions ,Dissolution ,Powder diffraction ,Thiazide ,Eutectic system ,Nuclear chemistry ,medicine.drug - Abstract
The mechanochemical synthesis of drug–drug solid forms containing metformin hydrochloride (MET·HCl) and thiazide diuretics hydrochlorothiazide (HTZ) or chlorothiazide (CTZ) is reported. Characterization of these new systems indicates formation of binary eutectic conglomerates, i.e., drug–drug eutectic solids (DDESs). Further analysis by construction of binary diagrams (DSC screening) exhibited the characteristic V-shaped form indicating formation of DDESs in both cases. These new DDESs were further characterized by different techniques, including thermal analysis (DSC), solid state NMR spectroscopy (SSNMR), powder X-ray diffraction (PXRD) and scanning electron microscopy–energy dispersive X-ray spectroscopy analysis (SEM–EDS). In addition, intrinsic dissolution rate experiments and solubility assays were performed. In the case of MET·HCl-HTZ (χMET·HCl = 0.66), we observed a slight enhancement in the dissolution properties compared with pure HTZ (1.21-fold). The same analysis for the solid forms of MET·HCl-CTZ (χMET·HCl = 0.33 and 0.5) showed an enhancement in the dissolved amount of CTZ accompanied by a slight improvement in solubility. From these dissolution profiles and saturation solubility studies and by comparing the thermodynamic parameters (ΔHfus and ΔSfus) of the pure drugs with these new solid forms, it can be observed that there was a limited modification in these properties, not modifying the free energy of the solution (ΔG) and thus not allowing an improvement in the dissolution and solubility properties of these solid forms.
- Published
- 2021
12. Mechanochemistry: A Green Approach in the Preparation of Pharmaceutical Cocrystals
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David Morales-Morales, Guadalupe Coyote-Dotor, Daniel Canseco-González, Miriam Rosario Zermeño-Ortega, Mizraín Solares-Briones, José C. Páez-Franco, Carmen Myriam de la O Contreras, Juan Manuel Germán-Acacio, and Alcives Avila-Sorrosa
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Solvent free ,green reactions ,010405 organic chemistry ,Pharmaceutical Science ,Nanotechnology ,Review ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,RS1-441 ,chemistry.chemical_compound ,Pharmacy and materia medica ,chemistry ,Mechanochemistry ,Organic synthesis ,mechanochemistry ,pharmaceutical cocrystals - Abstract
Mechanochemistry is considered an alternative attractive greener approach to prepare diverse molecular compounds and has become an important synthetic tool in different fields (e.g., physics, chemistry, and material science) since is considered an ecofriendly procedure that can be carried out under solvent free conditions or in the presence of minimal quantities of solvent (catalytic amounts). Being able to substitute, in many cases, classical solution reactions often requiring significant amounts of solvents. These sustainable methods have had an enormous impact on a great variety of chemistry fields, including catalysis, organic synthesis, metal complexes formation, preparation of multicomponent pharmaceutical solid forms, etc. In this sense, we are interested in highlighting the advantages of mechanochemical methods on the obtaining of pharmaceutical cocrystals. Hence, in this review, we describe and discuss the relevance of mechanochemical procedures in the formation of multicomponent solid forms focusing on pharmaceutical cocrystals. Additionally, at the end of this paper, we collect a chronological survey of the most representative scientific papers reporting the mechanochemical synthesis of cocrystals.
- Published
- 2021
13. Synthesis and characterisation of magnetite nanoparticles using gelatin and starch as capping agents
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Daniel Canseco-González, Teodoro Espinosa-Solares, Flor de María Guerrero-Toledo, Guadalupe Stefanny Aguilar-Moreno, Elizabeth Navarro-Cerón, Miguel A. Aguilar-Méndez, and Azucena Velázquez-Hernández
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Materials science ,food.ingredient ,Starch ,Nanoparticle ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,Gelatin ,Colloid ,chemistry.chemical_compound ,food ,Dynamic light scattering ,X-Ray Diffraction ,Zeta potential ,Electrical and Electronic Engineering ,Fourier transform infrared spectroscopy ,Particle Size ,Magnetite Nanoparticles ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Electronic, Optical and Magnetic Materials ,chemistry ,Magnetic nanoparticles ,0210 nano-technology ,Biotechnology ,Nuclear chemistry ,Research Article - Abstract
Nanoparticles of magnetite passivated with gelatin and starch were synthesised using a co-precipitation technique. The nanoparticles were characterised using ultraviolet-visible (UV-vis), dynamic light scattering (DLS), Zeta potential, transmission electron microscope (TEM), X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FTIR). The UV-vis spectra showed characteristic surface plasmon resonance of magnetite nanoparticles. The DLS results showed the nanoparticles to have average hydrodynamic diameters of 138 ± 2 and 283 ± 21 nm for particles passivated with gelatin and starch, respectively. The stability in a colloidal solution was greater in nanoparticles passivated with gelatin than nanoparticles obtained with starch, as can be seen by their Zeta potential value (-31 ± 2 and -16 ± 0.5 mV, respectively). According to the TEM evaluation, the use of gelatin allowed to obtain nanoparticles with a spherical morphology and an average size of 10 ± 2 nm. However, when using starch the nanoparticles exhibited diverse morphologies with an average size of 25 ± 7 nm. The XRD results confirmed the crystalline structure of the samples, which showed crystallite sizes of 14.90 and 24.43 nm for nanoparticles passivated with gelatin and starch, respectively. FTIR analysis proved the establishment of interactions between functional groups of biopolymers and magnetite nanoparticles.
- Published
- 2020
14. C-S cross-coupling reactions catalyzed by a non-symmetric phosphinito-thiophosphinito PSCOP-Ni(II) pincer complex
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Daniel Canseco-González, Juan Manuel Serrano-Becerra, Valente Gómez-Benítez, David Morales-Morales, Hugo Valdés, and Simón Hernández-Ortega
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010405 organic chemistry ,Chemistry ,Organic Chemistry ,Center (category theory) ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Coupling reaction ,0104 chemical sciences ,Catalysis ,Pincer movement ,Crystallography ,Iodobenzenes ,Drug Discovery ,Molecule ,Selectivity ,Single crystal - Abstract
A new non-symmetric phosphinito-thiophosphinito POCSP-Ni(II) pincer compound was synthetized and characterized. The molecular structure of [NiCl{C6H3-2-(OPPh2)-6-(SPPh2)}] (1) was unequivocally determined by single crystal X-ray diffraction analysis, showing the Ni center to be located into a slightly distorted square planar geometry. This compound was used as efficient catalyst in C-S couplings of disulfides with iodobenzenes, exhibiting good activity and selectivity as well as tolerance to different functional groups.
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- 2018
15. Respuesta Numérica deChilocorus cactiSobreDactylopius opuntiae
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Jaime Daniel Canseco González, Alfonso Luna Cruz, Irma Sánchez Cabrera, Samuel Ramírez Alarcón, Evert Villanueva Sánchez, and Clemente Villanueva Verduzco
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0106 biological sciences ,010602 entomology ,Ecology ,Insect Science ,Biology ,01 natural sciences ,Agronomy and Crop Science ,Humanities ,010606 plant biology & botany - Abstract
La respuesta numerica de Chilocorus cacti Linnaeus, 1767 (Coleoptera: Coccinellidae), como depredador de la cochinilla silvestre (Dactylopius opuntiae (Cockerell)), se determino a traves de estudios en laboratorio. Al cuantificar la dinamica de la respuesta numerica, se encontro que al aumentar la cantidad de presas ofrecidas, el depredador incremento el numero de huevos ovipositados y de presas depredadas. Segun las regresiones lineales simples realizadas: por cada dos presas ofrecidas, se incremento el numero de huevos ovipositados en 1.238 y el numero de presas depredadas en 0.554; y el numero de huevos ovipositados se incremento en 0.636 por cada dos presas depredadas.
- Published
- 2018
16. Recent Advances in Catalysis with Transition-Metal Pincer Compounds
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David Morales-Morales, Marco A. García-Eleno, Daniel Canseco-González, and Hugo Valdés
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010405 organic chemistry ,Chemistry ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,Catalysis ,0104 chemical sciences ,Pincer movement ,Inorganic Chemistry ,Hydrogen storage ,Transition metal ,Dehydrogenation ,Physical and Theoretical Chemistry - Published
- 2018
17. Gold catalysis in organic transformations: A review
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Sohail Anjum Shahzad, Muhammad Aamir Sajid, Zulfiqar Ali Khan, and Daniel Canseco-González
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010405 organic chemistry ,Chemistry ,Organic Chemistry ,Nanotechnology ,Active systems ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,Organic reaction ,Wide area ,Organic synthesis ,Reusability - Abstract
This review updates the explosive development of gold catalysis for organic transformation focusing on the current literature over last 3 years. Recent investigations have shown that gold catalysis provides catalytically active systems, whereas selectivity and reusability are advantages over noncatalyzed organic transformations. The collected literature is focusing for new organic reactions and synthetic methodologies. Gold can also be suggested for green processes dedicated to fine chemicals, pharmaceuticals, and the food industry due to its recognized biocompatibility. The current review is focused on new methods in the organic synthesis that could be of interest in the wide area of organic chemistry for developing new catalytic pathways.
- Published
- 2017
18. Benzene-Derived Organometallic Pincer Compounds Bearing Six-Membered Metallacycles and Up
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Lucero González-Sebastián, David Morales-Morales, and Daniel Canseco-González
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chemistry.chemical_compound ,Bearing (mechanical) ,law ,Chemistry ,Metalation ,Benzene ,Combinatorial chemistry ,law.invention ,Pincer movement ,Catalysis - Abstract
This chapter describes the chemistry of pincer compounds including metallacycles larger than 5, i.e., 6 and 7 membered, the synthetic procedures for the attaining of the ligands, and metalation procedures to produce the corresponding complexes. The consequences of increasing the size of the metallacycles are also discussed both in terms of structure of the complexes and their effects in catalysis when the complexes were designed or employed for these purposes in different transformations.
- Published
- 2018
19. NHC-Ir(I) complexes derived from 5,6-dinitrobenzimidazole. Synthesis, characterization and preliminary evaluation of their in vitro anticancer activity
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Simón Hernández-Ortega, David Morales-Morales, Antonio Nieto-Camacho, Hugo Valdés, Arturo Sánchez-Mora, María Teresa Ramírez-Apan, and Daniel Canseco-González
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010405 organic chemistry ,Prostatic adenocarcinoma ,Chemistry ,010402 general chemistry ,Ligand (biochemistry) ,medicine.disease ,01 natural sciences ,Molecular biology ,In vitro ,0104 chemical sciences ,Inorganic Chemistry ,Materials Chemistry ,medicine ,Ic50 values ,Adenocarcinoma ,Colorectal adenocarcinoma ,Physical and Theoretical Chemistry ,Human cancer ,Glioblastoma - Abstract
The design, synthesis, characterization and in vitro anticancer activity of a series of Ir(I) NHC complexes derived from 5,6-dinitrobenzimidazole is reported. The evaluation was performed in five human cancer cell-lines, namely glioblastoma (U-251), prostatic adenocarcinoma (PC-3), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7) and lung adenocarcinoma (SKLU-7), including healthy cells of African green monkey kidney (COS-7) for comparative purposes. The complexes exhibited better activity in comparison with the corresponding NHC ligand precursors. In particular, complex (4a) exhibited a good performance against PC-3 and SKLU-1 with IC50 values of 10.6 ± 0.9 μM and 10.4 ± 1.5 μM, respectively.
- Published
- 2019
20. ChemInform Abstract: Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate
- Author
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Cathleen M. Crudden, Daniel Canseco-González, D. Dawson Beattie, Masakazu Nambo, and Zachary T. Ariki
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chemistry.chemical_compound ,chemistry ,chemistry.chemical_element ,General Medicine ,Scandium ,Trifluoromethanesulfonate ,Combinatorial chemistry ,Catalysis ,Sulfone - Abstract
A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.
- Published
- 2016
21. Crystal structure of 1-mesityl-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium iodide
- Author
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Marcos Flores-Alamo, Juventino J. García, and Daniel Canseco-González
- Subjects
chemistry.chemical_classification ,crystal structure ,Crystallography ,triazolium salt ,Hydrogen bond ,Chemistry ,Iodide ,Salt (chemistry) ,mesityl group ,General Chemistry ,Crystal structure ,Condensed Matter Physics ,Bioinformatics ,Ring (chemistry) ,Data Reports ,Crystal ,C—H⋯I hydrogen bonds ,QD901-999 ,General Materials Science ,C—H...I hydrogen bonds - Abstract
In the cation of the title salt, C18H20N3+·I−, the mesityl and phenyl rings are inclined to the central triazolium ring by 61.39 (16) and 30.99 (16)°, respectively, and to one another by 37.75 (15)°. In the crystal, molecules are linkedviaC—H...I hydrogen bonds, forming slabs parallel to theabplane. Within the slabs there are weak π–π interactions present involving the mesityl and phenyl rings [inter-centroid distances are 3.8663 (18) and 3.8141 (18) Å].
- Published
- 2015
22. A highly active two six-membered phosphinite palladium PCP pincer complex [PdCl{C6H3(CH2OPPri)2-2,6}]
- Author
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Seyyed Javad Sabounchei, Ali Naghipour, David Morales-Morales, Daniel Canseco-González, and Craig M. Jensen
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Phosphinite ,chemistry.chemical_element ,Medicinal chemistry ,Pincer movement ,Catalysis ,Inorganic Chemistry ,Ring size ,chemistry.chemical_compound ,chemistry ,Heck reaction ,Materials Chemistry ,Organic chemistry ,Physical and Theoretical Chemistry ,Benzene ,Phosphine ,Palladium - Abstract
The diphosphinite 1,3-bis[(di-isopropylphosphinite)methyl]benzene (2) has been synthesized and its complexation in palladium chemistry investigated. Complex 3 represents the first example of a two six-member PCP pincer bis(phosphinite) species. A catalytic study of 3 in the Heck reaction, revealed this specie to have an outstanding activity in the olefination of iodo-, bromo- and chloro-benzenes. When compared with other PCP pincer complexes, the results show that both by increasing the ring size from five to six-membered and using phosphinite instead of phosphine groups lead to a more active catalyst.
- Published
- 2007
23. List of Contributors
- Author
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Matthew Asay, Maravanji S. Balakrishna, Wesley H. Bernskoetter, Benoît Bertrand, Manfred Bochmann, Sarote Boonseng, Kristin Bowman-James, Juan Cámpora, Daniel Canseco-González, Ivan Castillo, Adrian B. Chaplin, Basujit Chatterjee, Xiangyang Chen, Gunanathan Chidambaram, Jong-Hoo Choi, Hans P. Cook, Hazel Cox, Peng Cui, Jason A. Denny, Tara K.K. Dickie, Alejandro Dorazco-González, Libor Dostál, Nathan A. Eberhardt, Miguel A. Esteruelas, Huaquan Fang, Julio Fernandez-Cestau, Michael Findlater, Jun-Fang Gong, Lucero González-Sebastián, Nikolaus Gorgas, Hairong Guan, Rajeev Gupta, Go Hamasaka, Paul G. Hayes, Nilay Hazari, T. Keith Hollis, Zheng Huang, Kengo Hyodo, Vlad M. Iluc, Jun-ichi Ito, Roman Jambor, William D. Jones, Sandeep Kaur, Karl Kirchner, Naveen V. Kulkarni, Pramod Kumar, Georgette M. Lang, Guixia Liu, Connor S. MacNeil, Virginia Montiel-Palma, David Morales-Morales, Shuichi Nakamura, Hisao Nishiyama, Montserrat Oliván, Pilar Palma, Dennis Pingen, Martin H.G. Prechtl, Latchupatula Radhakrishna, Luca Rocchigiani, Antonio Rodríguez-Delgado, Gavin Roffe, Anu Saini, Eduardo Sola, Mao-Ping Song, John Spencer, Caroline M. Storey, Yasuhiro Uozumi, Hugo Valdés, Jarl Ivar van der Vlugt, Gerard van Koten, Ola F. Wendt, Xinzheng Yang, Julio Zamora-Moreno, and Xinju Zhu
- Published
- 2015
24. Tandem transmetallation and oxidative addition reactions of [Sn(R)2(Ph2PC6H4-2-S)2] with transition metal complexes of the Group 9
- Author
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David Morales-Morales, Simón Hernández-Ortega, Valente Gómez-Benítez, Daniel Canseco-González, and Oscar Baldovino-Pantaleón
- Subjects
Stereochemistry ,Organic Chemistry ,chemistry.chemical_element ,Crystal structure ,Biochemistry ,Medicinal chemistry ,Oxidative addition ,Rhodium ,Inorganic Chemistry ,Transmetalation ,chemistry.chemical_compound ,chemistry ,Transition metal ,Octahedron ,Materials Chemistry ,Iridium ,Physical and Theoretical Chemistry ,Derivative (chemistry) - Abstract
The reactions of [Sn(Ph)2(Ph2PC6H4-2-S)2] with trans -[M(Cl)(CO)(PPh3)2] M=Ir, Rh afford the complexes [Rh(Ph2PC6H4-2-S)2(SnClPh2)] (1) and [Ir(CO)(Ph2PC6H4-2-S)2(SnClPh2)] (2) as final products of two processes, a transmetallation reaction and an oxidative addition process. The crystal structures of both complexes have been determined, showing the rhodium compound to be into a slightly distorted square base pyramidal geometry, while that of the iridium derivative can be described as a distorted octahedron.
- Published
- 2004
25. Transmetallation reactions of [Sn(R)2(Ph2PC6H4-2-S)2] with metal complexes of the Group 10
- Author
-
David Morales-Morales, Valente Gómez-Benítez, Daniel Canseco-González, Simón Hernández-Ortega, and Rubén A. Toscano
- Subjects
Steric effects ,Stereochemistry ,Organic Chemistry ,Aromaticity ,Crystal structure ,Biochemistry ,Medicinal chemistry ,Inorganic Chemistry ,Metal ,chemistry.chemical_compound ,Transmetalation ,chemistry ,visual_art ,Materials Chemistry ,visual_art.visual_art_medium ,Moiety ,Stereoselectivity ,Physical and Theoretical Chemistry ,Phosphine - Abstract
The complexes cis -[M(Ph 2 PC 6 H 4 -2-S) 2 ] M=Ni, Pd, Pt were stereoselectively synthesized by transmetallation reactions of [M(Cl) 2 (NCC 6 H 5 ) 2 ] M=Pd, Pt or NiCl 2 ·6H 2 O with [Sn(R) 2 (Ph 2 PC 6 H 4 -2-S) 2 ] R=Ph, n Bu or t Bu. The conformation of the Pd and Pt derivatives being unequivocally confirmed by single crystal X-ray diffraction studies showing both metal centers to be into a slightly distorted square planar environment, the main distortion being due to the steric hindrance caused by the aromatic rings in the phosphine moiety.
- Published
- 2003
26. ChemInform Abstract: Carbene Transfer from Triazolylidene Gold Complexes as a Potent Strategy for Inducing High Catalytic Activity
- Author
-
Kohsuke Ohmatsu, Daniel Canseco-González, Takashi Ooi, Helge Mueller-Bunz, Ana Petronilho, and Martin Albrecht
- Subjects
In situ ,chemistry.chemical_compound ,chemistry ,Cationic polymerization ,General Medicine ,Combinatorial chemistry ,Carbene ,Catalysis - Abstract
Catalytically active cationic complexes generated in situ from newly synthesized gold(I) complexes containing triazolylidene ligands in combination with AgBF4 are used as effective catalysts in the reaction of isocyanides and aldehydes to form oxazolines.
- Published
- 2014
27. Synthesis and catalytic alcohol oxidation and ketone transfer hydrogenation activity of donor-functionalized mesoionic triazolylidene ruthenium(II) complexes
- Author
-
Manuela Hollering, Martin Albrecht, Helge Mueller-Bunz, Manuela Delgado-Rebollo, and Daniel Canseco-González
- Subjects
chemistry.chemical_classification ,Ketone ,chemistry.chemical_element ,Transfer hydrogenation ,Medicinal chemistry ,Solvento complexes ,Ruthenium ,Catalysis ,Inorganic Chemistry ,Direct alcohol oxidation ,chemistry.chemical_compound ,chemistry ,Ruthenium cymene complexes ,Pyridine ,Alkoxide ,Organic chemistry ,Dehydrogenation ,Carboxylate ,Ketone transfer hydrogenation - Abstract
We report on the synthesis of a variety of C,E-bidentate triazolylidene ruthenium complexes that comprise different donor substituents E (E=C: phenyl anion; E=O: carboxylate, alkoxide; E=N: pyridine at heterocyclic carbon or nitrogen). Introduction of these donor functionalities is greatly facilitated by the synthetic versatility of triazoles, and their facile preparation routes. Five different complexes featuring a C,E-coordinated ruthenium center with chloride/cymene spectator ligands and three analogous solvento complexes with MeCN spectator ligands were prepared and evaluated as catalyst precursors for direct base- and oxidant-free alcohol dehydrogenation, and for transfer hydrogenation using basic iPrOH as a source of dihydrogen. In both catalytic reactions, the neutral/mono-cationic complexes with chloride/cymene spectator ligands performed better than the solvento ruthenium complexes. The donor functionality had a further profound impact on catalytic activity. For alcohol dehydrogenation, the C,C-bidentate phenyl-triazolylidene ligand induced highest conversions, while carboxylate or pyridine donor sites gave only moderate activity or none at all. In contrast, transfer hydrogenation is most efficient when a pyridyl donor group is linked to the triazolylidene via the heterocyclic carbon atom, providing turnover frequencies as high as 1400 h-1 for cyclohexanone transfer hydrogenation. The role of the donor group is discussed in mechanistic terms. European Research Council Science Foundation Ireland
- Published
- 2014
28. Carbene transfer from triazolylidene gold complexes as a potent strategy for inducing high catalytic activity
- Author
-
Ana Petronilho, Takashi Ooi, Martin Albrecht, Daniel Canseco-González, Kohsuke Ohmatsu, and Helge Mueller-Bunz
- Subjects
Models, Molecular ,Stereochemistry ,Crystallography, X-Ray ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,Catalysis ,chemistry.chemical_compound ,Colloid and Surface Chemistry ,Redistribution (chemistry) ,Molecular Structure ,010405 organic chemistry ,Ligand ,Cationic polymerization ,General Chemistry ,Triazoles ,0104 chemical sciences ,IMes ,chemistry ,Precious metals ,Aldol condensation ,Methane ,Organogold Compounds ,Carbene - Abstract
A series of gold(I) complexes [AuCl(trz)] were synthesized that contain 1,2,3-triazolylidene (trz) ligands with variable wingtip groups. In the presence of AgBF4, these complexes undergo ligand redistribution to yield cationic complexes [Au(trz)2]BF4 in high yields as a result of efficient carbene transfer. Identical reactivity patterns were detected for carbene gold complexes comprised of Arduengo-type IMes ligands (IMes=N,N⠲-dimesityl-imidazol-2-ylidene). Reaction of cationic complexes [Au(trz)2]+ with [AuCl(trz⠲)] afforded the heteroleptic complex [Au(trz)(trz⠲)]+ and [AuCl(trz)] (trz, trz⠲=triazolylidene ligands with different wingtip groups). Carbene transfer occurs spontaneously, yet is markeldy rate-enhanced in the presence of Ag+. The facile carbene transfer was exploited as a catalyst activation process to form active gold species for the aldol condensation of isocyanides and aldehydes to form oxazolines. The catalytic activity is strongly dependent on the presence of Ag+ ions to initiate catalyst activation. High turnovers (105) and turnover frequencies (10 4 h-1) were accomplished. Structural analysis at early stages of the reaction support the critical role of triazolylidene dissociation to activate the precatalyst and dynamic light scattering revealed the presence of nanoparticles (±100 nm diameter) as potential catalytically active species. Furthermore, the triazolylidene scaffold had no impact on the diastereoselectivity of the oxazoline formation, and chiral triazolylidenes did not induce any asymmetry in the product. The facile dissociation of carbenes from [AuCl(carbene)] in the presence of Ag+ ions suggests a less stable Au-Ccarbene interaction than often assumed, with potential implications for gold-catalyzed reactions that employ a silver salt as (putative) halide scavenger. European Research Council Science Foundation Ireland JSPS Funding Program for Next Generation World-Leading Researchers
- Published
- 2013
29. PEPPSI-type palladium complexes containing basic 1,2,3-triazolylidene ligands and their role in Suzuki-Miyaura catalysis
- Author
-
Helge Müller-Bunz, Martin Albrecht, Michał S. Szulmanowicz, Daniel Canseco-González, Anna M. Trzeciak, and Andrzej Gniewek
- Subjects
inorganic chemicals ,Mesoionic carbene ,chemistry.chemical_element ,Homogeneous catalysis ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Catalysis ,chemistry.chemical_compound ,Polymer chemistry ,Heterogeneous catalysis ,010405 organic chemistry ,Ligand ,Aryl ,Organic Chemistry ,Mesoionic ,General Chemistry ,0104 chemical sciences ,PEPPSI ,chemistry ,Spectator ligand ,Cross-coupling ,Palladium - Abstract
A series of PEPPSI-type palladium(II) complexes was synthesized that contain 3-chloropyridine as an easily removable ligand and a triazolylidene as a strongly donating mesoionic spectator ligand. Catalytic tests in Suzuki–Miyaura cross-coupling reactions revealed the activity of these complexes towards aryl bromides and aryl chlorides at moderate temperatures (50 °C). However, the impact of steric shielding was the inverse of that observed with related normal Nheterocyclic carbenes (imidazol-2-ylidenes) and sterically congested mesityl substituents induced lower activity than small alkyl groups. Mechanistic investigations, including mercury poisoning experiments, TEM analyses, and ESI mass spectrometry, provide evidence for ligand dissociation and the formation of nanoparticles as a catalyst resting state. These heterogeneous particles provide a reservoir for soluble palladium atoms or clusters as operationally homogeneous catalysts for the arylation of aryl halides. Clearly, the substitution of a normal N-heterocyclic carbene for a more basic triazolylidene ligand in the precatalyst has a profound impact on the mode of action of the catalytic system. European Research Council Science Foundation Ireland
- Published
- 2011
30. Synthesis and Tunability of Abnormal 1,2,3-Triazolylidene Palladium and Rhodium Complexes
- Author
-
Antonia Neels, Daniel Canseco-González, Martin Albrecht, Helge Müller-Bunz, Helen Stoeckli-Evans, Rachel Hynes-Roche, Oliver Schuster, and Aurélie Poulain
- Subjects
Cyclopalladation ,Metalation ,Organic Chemistry ,chemistry.chemical_element ,Metathesis ,Photochemistry ,Rhodium ,Triazolylium salts ,Inorganic Chemistry ,chemistry.chemical_compound ,Transmetalation ,chemistry ,Triazolylidene ligand ,Polymer chemistry ,Rhodium complexes ,Palladium complexes ,Physical and Theoretical Chemistry ,Carbene ,Bimetallic strip ,Cis–trans isomerism ,Palladium - Abstract
Palladation of N3-alkylated 1,2,3-triazolium salts with Pd(OAc)2 afforded a μ2−I2 bridged bimetallic complex [Pd(trz)I2]2 and monometallic bis(carbene) complexes Pd(trz)2I2 as a mixture of trans and cis isomers (trz = 1,2,3-triazol-5-ylidene). Addition of excess halide or modification of the palladation procedure from direct functionalization to a transmetalation sequence involving a silver intermediate allowed for chemoselective formation of the bis(carbene) complex, while subsequent anion metathesis with NaI produced the monometallic bis(carbene) complexes exclusively. Modification of the wingtip group had little influence on the metalation to palladium or rhodium(I) via transmetalation. According to NMR analysis using δC and 1JRh−C, subtle but noticeable tunability of the metal electronic properties was identified. In addition, phenyl wingtip groups as N-substituents in the triazolylidene ligands were susceptible to cyclopalladation in the presence of NaOAc and are thus not chemically inert. University College Dublin Swiss National Science Foundation Marie-Curie IEF Alfred Werner Foundation
- Published
- 2011
Catalog
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