Search

Your search keyword '"Marcelo Murguia"' showing total 2 results
Start Over Author "Marcelo Murguia" Search Limiters Available in Library Collection
2 results on '"Marcelo Murguia"'

1. Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs

Author

Raquel Román, Juan F. Sanz-Cervera, Salvador Villanova, Santos Fustero, Ana C. Cuñat, Marcelo Murguia, and Antonio Simón-Fuentes

Subjects
Methylhydrazine, FLUORINATED PYRAZOL, Fluorine Compounds, Alcohol, Pyrazole, Methylation, Chemical synthesis, PYRAZOL, chemistry.chemical_compound, Animals, Organic chemistry, Acari, Diketone, Tebufenpyrad, Molecular Structure, Chemistry, Organic Chemistry, Ciencias Químicas, Regioselectivity, Stereoisomerism, FLUOROUS, Phenylhydrazines, Solvent, Química Orgánica, Alcohols, Solvents, Pyrazoles, TEBUFENPYRAD, CIENCIAS NATURALES Y EXACTAS
Abstract

The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity. Fil: Fustero, Santos. Universidad de Valencia; España Fil: Roman, Raquel. Universidad de Valencia; España Fil: Sanz Cervera, Juan F.. Universidad de Valencia; España. Centro de Investigaciones Principe Felipe; España Fil: Simon Fuentes, Antonio. Universidad de Valencia; España Fil: Cuñat, Ana. Universidad de Valencia; España Fil: Villanova, Salvador. Universidad de Valencia; España Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina

Published
2008

2. Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies

Author

Raúl Mínguez Blasco, Juan F. Sanz-Cervera, Michael H. Cynamon, Santos Fustero, Julio Piera, Ignacio Ibáñez, and Marcelo Murguia

Subjects
Azoles, Staphylococcus aureus, ANTIBACTERIAL ACTIVITY, Drug Evaluation, Preclinical, Microbial Sensitivity Tests, Chemical synthesis, Small Molecule Libraries, Acylation, chemistry.chemical_compound, Solid-phase synthesis, Column chromatography, AZOLES, Organic chemistry, Moiety, Antibacterial agent, Chemistry, Organic Chemistry, Ciencias Químicas, FLUOROUS, Combinatorial chemistry, Anti-Bacterial Agents, Solutions, Química Orgánica, Molecular Probes, SOLID-PHASE, Lawesson's reagent, Antibacterial activity, CIENCIAS NATURALES Y EXACTAS
Abstract

A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate α-amido-β-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson’s reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine with a fluorous tag in the ester moiety is used as a starting material, the synthesis can be easily completed without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus. Fil: Sanz Cervera, Juan F.. Universidad de Valencia; España Fil: Blasco, Raül. Universidad de Valencia; España Fil: Piera, Julio. Universidad de Valencia; España Fil: Cynamon, Michael. SUNY Upstate Medical University; Estados Unidos Fil: Ibáñez, Ignacio. Universidad de Valencia; España Fil: Murguia, Marcelo Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina Fil: Fustero, Santos. Universidad de Valencia; España

Published
2009

Catalog

Books, media, physical & digital resources
See catalog results