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Abstract:

Enantiomeric 2,3,4-tris(hydroxyalkyl)-5-phenylpyrrolidines have been synthesized from the major cycloadducts obtained by the 1,3-dipolar cycloaddition of sugar enones with azomethine ylides derived from natural amino acids. Reduction of the ketone carbonyl group of the cycloadducts, which possess a basic structure of bicyclic 6-(menthyloxy)hexahydropyrano[4,3-c]pyrrol-7(6H)one, afforded a number of pyrrolidine-based bicyclic systems. A sequence of reactions, which involved hydrolysis of the menthyloxy substituent, reduction, N-protection, and degradative oxidation, afforded varied pyrrolidine structures having diverse configurations and patterns of substitution; in particular, polyhydroxylated derivatives have been obtained. The unprotected products were isolated as pyrrolidinium trifluoroacetates. Because of the furanose-like nature of the target trihydroxyalkyl pyrrolidines, these molecules have been evaluated as inhibitors of the β-galactofuranosidase from Penicillium fellutanum. The compounds showed practically no inhibitory activity for concentration of pyrrolidines in the range of 0.1-1.6 mM. © 2016 American Chemical Society.

Registro:

Documento: Artículo
Título:Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase
Autor:Oliveira Udry, G.A.; Repetto, E.; Vega, D.R.; Varela, O.
Filiación:CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Departamento Física de la Materia Condensada, GAIyANN-CAC-CNEA y ECyT-UNSAM, Av. Gral. Paz 1499, San Martín, Buenos Aires, 1650, Argentina
Palabras clave:Ketones; 1 ,3-Dipolarcycloaddition; Azomethine ylides; Bicyclic systems; Carbonyl groups; Natural amino acids; No inhibitory activities; Polyhydroxylated; Trifluoroacetates; Enantiomers; azomethine ylide; carbonyl derivative; glycosidase; ketone derivative; pyrrolidine derivative; bridged bicyclo compounds; enzyme inhibitor; exo-beta-D-galactofuranosidase; pyrrolidine derivative; Article; chemical structure; cycloaddition; enantiomer; enzyme inhibition; hydrolysis; molecule; nonhuman; oxidation; Penicillium; reduction; substitution reaction; synthesis; antagonists and inhibitors; conformation; drug effect; enzymology; molecular model; oxidation reduction reaction; stereoisomerism; Bridged Bicyclo Compounds; Cycloaddition Reaction; Enzyme Inhibitors; Glycoside Hydrolases; Hydrolysis; Models, Molecular; Molecular Conformation; Oxidation-Reduction; Penicillium; Pyrrolidines; Stereoisomerism
Año:2016
Volumen:81
Número:10
Página de inicio:4179
Página de fin:4189
DOI: http://dx.doi.org/10.1021/acs.joc.6b00514
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:azomethine ylide, 107081-71-0, 1761-67-7, 176903-89-2; glycosidase, 9032-92-2; Bridged Bicyclo Compounds; Enzyme Inhibitors; exo-beta-D-galactofuranosidase; Glycoside Hydrolases; Pyrrolidines
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v81_n10_p4179_OliveiraUdry

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Citas:

---------- APA ----------
Oliveira Udry, G.A., Repetto, E., Vega, D.R. & Varela, O. (2016) . Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase. Journal of Organic Chemistry, 81(10), 4179-4189.
http://dx.doi.org/10.1021/acs.joc.6b00514
---------- CHICAGO ----------
Oliveira Udry, G.A., Repetto, E., Vega, D.R., Varela, O. "Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase" . Journal of Organic Chemistry 81, no. 10 (2016) : 4179-4189.
http://dx.doi.org/10.1021/acs.joc.6b00514
---------- MLA ----------
Oliveira Udry, G.A., Repetto, E., Vega, D.R., Varela, O. "Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase" . Journal of Organic Chemistry, vol. 81, no. 10, 2016, pp. 4179-4189.
http://dx.doi.org/10.1021/acs.joc.6b00514
---------- VANCOUVER ----------
Oliveira Udry, G.A., Repetto, E., Vega, D.R., Varela, O. Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase. J. Org. Chem. 2016;81(10):4179-4189.
http://dx.doi.org/10.1021/acs.joc.6b00514