Persona: Nieto Gómez, Carla Isabel
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Nieto Gómez
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Publicación Effects of Curcuminoid Pyrazoles on Cancer Cells and on the Expression of Telomerase Related Genes(Wiley, 2016-07) Martí Centelles, Rosa; Falomir Ventura, Eva; Carda, Miguel; Cornago, María del Pilar; Claramunt, Rosa María; Nieto Gómez, Carla IsabelA group of 13 curcuminoid pyrazoles was investigated for their cytotoxicity on three tumoral cell lines (HT-29, MCF-7, and HeLa) and one non-tumoral human cell line (HEK-293). The values obtained were compared with those of curcumin. A subset of selected derivatives was also studied for their ability to downregulate expression of the hTERT and c-Myc genes, which are both involved in telomerase activity.Publicación Reconocimiento molecular de pirazoles e imidazoles(Universidad Nacional de Educación a Distancia (España). Facultad de Ciencias. Departamento de Química Orgánica y Bio-Orgánica, 2011-07-06) Nieto Gómez, Carla IsabelEn los últimos años el diseño de receptores moleculares para el reconocimiento selectivo de moléculas de importancia biológica y/o química ha cobrado gran importancia, lo que ha incentivado el estudio en profundidad del reconocimiento molecular. El reconocimiento molecular abarca un conjunto de fenómenos controlados por interacciones específicas y de naturaleza no covalente. Un reconocimiento efectivo entre especies moleculares (moléculas neutras o iones) implica la existencia de interacciones y requerimientos espaciales entre ambas especies para cumplir un determinado fin o función. Por tanto, en el diseño de receptores moleculares hay que tener en cuenta factores como la complementariedad espacial y química entre receptor y sustrato, la interacción electrostática, las interacciones Pi-Pi de apilamiento aromático, las atracciones de van der Waals entre regiones hidrofóbicas de ambas especies y, de manera particular, las interacciones mediante enlace de hidrógeno entre átomos electronegativos. Recientemente también han cobrado importancia las interacciones atractivas entre otros átomos como halógenos o fósforo. Aunque se ha avanzado mucho en el conocimiento de las reglas fundamentales que rigen el reconocimiento molecular, existen hoy en día dos líneas de investigación en este ámbito bien diferenciadas: el estudio de los procesos en disolución o química hostguest y el de las interacciones en estado sólido que constituyen la ingeniería cristalina.7 En el presente trabajo, que se enmarca en el campo de la ingeniería de cristales, se estudiará el reconocimiento molecular en estado sólido de seis azoles (1H-pirazol, 3,5- dimetil-1H-pirazol, 3,5-dimetil-4-nitro-1H-pirazol, 1H-imidazol, 2-metil-1H-imidazol y 4(5)-metil-1H-imidazol) por tres quinolinas (2,8-dihidroxiquinolina, 8-hidroxiquinolina y quinolin-2(1H)-ona), basándose en la metodología de los heterosintones supramoleculares. Los compuestos quinolínicos tanto de origen natural como sintético son de gran interés científico debido a sus propiedades biológicas, su gran potencial como agentes farmacéuticos y su actividad bioquímica. Es por ello, que el estudio de estos compuestos como receptores moleculares de azoles ofrece numerosas posibilidades en química médica, supramolecular y farmacéutica. Para este estudio se han empleado cuatro herramientas fundamentales: ‐ Métodos computacionales basados en la teoría del funcional de la densidad (DFT) a nivel B3LYP/6-311++G(d,p). ‐ Resonancia Magnética Nuclear (RMN) en estado sólido donde los desplazamientos químicos de 13C y 15N nos permiten caracterizar las interacciones moleculares de enlaces de hidrógeno: O-H···N, N-H···N, N-H···O y C-H···O. ‐ Difracción de rayos X que nos permitirá analizar la estructura molecular y los heterosintones supramoleculares responsables de la red cristalina. ‐ Calorimetría diferencial de barrido, mediante la cual se realizarán estudios de cocristales, polimorfismo y transiciones de fase. En resumen, el objetivo de este trabajo consiste en, a través de las técnicas anteriormente citadas, estudiar la posible discriminación de unos azoles frente a otros por parte de las quinolinas basándose en modelos fenol-piridona.Publicación The structure of β-diketones related to curcumin determined by X-ray crystallography, NMR (solution and solid state) and theoretical calculations(Springer, 2013-12-09) Nieto Gómez, Carla Isabel; Cabildo Miranda, María del Pilar; Claramunt, Rosa M.; Cornago, María del Pilar; Sanz, Dionisia; Torralba, M. Carmen; Torres, M. Rosario; Ferraro, Marta B.; Alkorta, Ibon; Marín Luna, Marta; Elguero, JoséStructural data are reported on sixteen ketoenols of β-diketones: solution NMR, solid-state NMR (CPMAS and MAS) and X-ray crystallography (four compounds, where three are new). The emphasis is on the tautomerism between both ketoenols, in solution and in the solid state. GIAO/B3LYP/6-311++G(d,p) and Quantum ESPRESSO (QE) calculations were used and compared. For average values, the GIAO/DMSO-PCM is enough, but splittings can only be approached by using QE. A case of rotational disorder has been analyzed. Some anomalies related to C–F bonds and to the C–CF3 group have been detected.Publicación A multinuclear magnetic resonance study of fluoro derivatives of hydroxybenzaldehydes(2015-06-06) Claramunt, Rosa María; Alkorta, Ibon; Elguero, J.; Sanz del Castillo, Dionisia; Nieto Gómez, Carla IsabelPublicación Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin(MDPI, 2015-08-28) Cabildo Miranda, Mª del Pilar; Cornago, María del Pilar; Sanz, D.; Claramunt, R. M.; Torralba, M. Carmen; Torres, M. Rosario; Elguero, J.; Garcia, J. A.; Acuña Castroviejo, Darío; Nieto Gómez, Carla Isabel; López Peláez, AntonioA series of new (E)-3(5)-[β-(aryl)-ethenyl]-5(3)-phenyl-1H-pyrazoles bearing fluorine atoms at different positions of the aryl group have been synthesized starting from the corresponding β-diketones. All compounds have been characterized by elemental analysis, DSC as well as NMR (1H, 13C, 19F and 15N) spectroscopy in solution and in solid state. Three structures have been solved by X-ray diffraction analysis, confirming the tautomeric forms detected by solid state NMR. The in vitro study of their inhibitory potency and selectivity on the activity of nNOS and eNOS (calcium-calmodulin dependent) as well as iNOS (calcium-calmodulin independent) isoenzymes is presented. A qualitative structure–activity analysis allowed the establishment of a correlation between the presence/absence of different substituents with the inhibition data proving that fluorine groups enhance the biological activity. (E)-3(5)-[β-(3-Fluoro-4-hydroxyphenyl)-ethenyl]-5(3)-phenyl-1H-pyrazole (13), is the best inhibitor of iNOS, being also more selective towards the other two isoforms.Publicación An experimental and theoretical NMR study of NH-benzimidazoles in solution and in the solid state: proton transfer and tautomerism(Beilstein-Institut, 2014) Nieto Gómez, Carla IsabelThis paper reports the 1H, 13C and 15N NMR experimental study of five benzimidazoles in solution and in the solid state (13C and 15N CPMAS NMR) as well as the theoretically calculated (GIAO/DFT) chemical shifts. We have assigned unambiguously the "tautomeric positions" (C3a/C7a, C4/C7 and C5/C6) of NH-benzimidazoles that, in some solvents and in the solid state, appear different (blocked tautomerism). In the case of 1H-benzimidazole itself we have measured the prototropic rate in HMPA-d18.Publicación Curcumin Related 1,4-Diazepines: Regioselective Synthesis, Structure Analysis, Tautomerism, NMR Spectroscopy, X-ray Crystallography, Density Functional Theory and GIAO Calculations(Wiley, 2017-05-02) Andrade, Ana; Claramunt, Rosa María; Torralba, M. Carmen; Torres, M. Rosario; Alkorta, Ibon; Elguero, J.; Nieto Gómez, Carla Isabel; Sanz del Castillo, DionisiaThe reaction of 1,2-ethylenediamine with seven fluorinated β-diketones affords two different 1,4-diazepine series depending on the experimental conditions. Their structures as well as tautomerism have been established by 1H, 13C, 15N and 19F nuclear magnetic resonance in solution supported by density functional theory calculations at the B3LYP/6-311++G(d,p) level. The two compounds obtained from (E)-5-(2-fluoro-4-hydroxyphenyl)-1-phenylpent-4-ene-1,3-dione were analyzed by X-ray crystallography and studied by solid-state NMR.Publicación Synthesis, structure and biological activity of 3(5)-trifluoromethyl-1H-pyrazoles derived from hemicurcuminoids(Elsevier, 2015-11-14) Cabildo Miranda, Mª del Pilar; Cornago, María del Pilar; Sanz, D.; Claramunt, R. M.; Alkorta, Ibon; Elguero, J.; Garcia, J. A.; Acuña Castroviejo, Darío; Nieto Gómez, Carla Isabel; López Peláez, AntonioSix new 3(5)-trifluoromethyl-5(3)-substituted-styryl-1H-pyrazoles have been synthesized and their tautomerism studied in solution and in the solid state. The determination of their structures has been based on multinuclear NMR spectroscopy together with GIAO/B3LYP/6–311++G(d,p) theoretical calculations of eight structures for each pyrazole (two tautomers and four conformations). Five out of the six compounds present inhibition percentages of the iNOS isoform higher than 50%. With regard to the nNOS inhibitory activity, only two of the studied compounds show an inhibition of about 50%. Finally, concerning the eNOS, there is a compound presenting a low percentage of inhibition (40.2%) attaining in the other cases 50%.Publicación X‑ray Molecular Structures of 23 N1-4-Nitrophenyl, 2,4- Dinitrophenyl, and 2,4,6-Trinitrophenyl-2-pyrazolines(American Chemical Society, 2023-01-03) Torralba, María del Carmen; Nieto Gómez, Carla Isabel; Claramunt Vallespí, Rosa María; Elguero, JoséHerein, we present a complete crystallographic study of three series of N1-aryl substituted-2-pyrazolines, the aryl group being 4-nitrophenyl (series1), 2,4-dinitrophenyl (series2), and 2,4,6-trinitrophenyl (series3). The structural features, bond distances and angles as well as torsions for each single compound will be described and comparatively discussed with data for related heterocycles found in the Cambridge Structural Database (2020.2.0). A deeper look at the data has been achieved to know the influence of the substituents on the molecular structures. In the crystals of compounds with stereogenic centers at positions 4 and 5, the presence of both enantiomers has been encountered in 12 cases out of 14 that include a literature result. Finally, molecular packings in all series have been analyzed reaching the conclusion that they follow several patterns depending on the existence or not, and the type of intermolecular interactions. A general pattern has been observed which implies a certain tendency of the molecules to arrange into chains, whose additional contacts could extend the dimensionality of the networkPublicación Synthesis, structure and NMR study of fluorinated isoxazoles derived from hemi-curcuminoids(Elsevier, 2019-03) Nieto Gómez, Carla Isabel; Cornago, María del Pilar; Cabildo, María del Pilar; Sanz del Castillo, Dionisia; Claramunt Vallespí, Rosa María; Elguero, JoséThe purpose of this work is to prepare a series of isoxazoles bearing phenyl and 4'-hydroxy-styryl substituents at position 3 and 5; besides the phenyl group of the styryl residue bears one or two fluorine substituents. They were prepared to study their structure in the solid state and in solution by X-ray crystallography and solid-state NMR (SSNMR) for the solid state and NMR for the solution. The reaction of hydroxylamine with hemi-curcuminoid β-diketones affords two isomeric isoxazoles we have named series a (3-phenyl) and b (5-phenyl) that have been identified and characterized. Four pairs have been prepared that in three cases bear one or two fluorine atoms. Three X-ray structures have been determined 3a, 3b and 5b; 3a crystallizes without solvent, 3b crystallizes with a water molecule hydrogen-bonded to a phenolic OH, finally 5b crystallizes as a solvate with a methanol molecule hydrogen-bonded to the isoxazole N atom. This hydrogen bond results in larger differences between 15N chemical shifts in DMSO-d6 solution and in the solid state. The splitting of some signals observed in Cross-Polarization Magic Angle Spinning (CPMAS) 13C NMR was assigned to 1JCF dipolar couplings. The combined use of crystallography and SSNMR affords a complete characterization of isomeric isoxazoles, in particular the assignment of an isoxazole to a or to b series is not a trivial matter. In this work, we describe methods for the synthesis of isoxazoles bearing fluorine substituents that are promising structures for drug discovery.