Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase

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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...

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Autor principal: Oliveira Udry, G.A
Otros Autores: Repetto, E., Vega, D.R, Varela, O.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: American Chemical Society 2016
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 scopus  |a 2-s2.0-84971324232 
024 7 |2 cas  |a 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 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a JOCEA 
100 1 |a Oliveira Udry, G.A. 
245 1 0 |a Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase 
260 |b American Chemical Society  |c 2016 
270 1 0 |m Varela, O.; CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Argentina; email: varela@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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520 3 |a 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.  |l eng 
593 |a 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 
593 |a Departamento Física de la Materia Condensada, GAIyANN-CAC-CNEA y ECyT-UNSAM, Av. Gral. Paz 1499, San Martín, Buenos Aires, 1650, Argentina 
690 1 0 |a KETONES 
690 1 0 |a 1 ,3-DIPOLARCYCLOADDITION 
690 1 0 |a AZOMETHINE YLIDES 
690 1 0 |a BICYCLIC SYSTEMS 
690 1 0 |a CARBONYL GROUPS 
690 1 0 |a NATURAL AMINO ACIDS 
690 1 0 |a NO INHIBITORY ACTIVITIES 
690 1 0 |a POLYHYDROXYLATED 
690 1 0 |a TRIFLUOROACETATES 
690 1 0 |a ENANTIOMERS 
690 1 0 |a AZOMETHINE YLIDE 
690 1 0 |a CARBONYL DERIVATIVE 
690 1 0 |a GLYCOSIDASE 
690 1 0 |a KETONE DERIVATIVE 
690 1 0 |a PYRROLIDINE DERIVATIVE 
690 1 0 |a BRIDGED BICYCLO COMPOUNDS 
690 1 0 |a ENZYME INHIBITOR 
690 1 0 |a EXO-BETA-D-GALACTOFURANOSIDASE 
690 1 0 |a PYRROLIDINE DERIVATIVE 
690 1 0 |a ARTICLE 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a CYCLOADDITION 
690 1 0 |a ENANTIOMER 
690 1 0 |a ENZYME INHIBITION 
690 1 0 |a HYDROLYSIS 
690 1 0 |a MOLECULE 
690 1 0 |a NONHUMAN 
690 1 0 |a OXIDATION 
690 1 0 |a PENICILLIUM 
690 1 0 |a REDUCTION 
690 1 0 |a SUBSTITUTION REACTION 
690 1 0 |a SYNTHESIS 
690 1 0 |a ANTAGONISTS AND INHIBITORS 
690 1 0 |a CONFORMATION 
690 1 0 |a DRUG EFFECT 
690 1 0 |a ENZYMOLOGY 
690 1 0 |a MOLECULAR MODEL 
690 1 0 |a OXIDATION REDUCTION REACTION 
690 1 0 |a STEREOISOMERISM 
690 1 0 |a BRIDGED BICYCLO COMPOUNDS 
690 1 0 |a CYCLOADDITION REACTION 
690 1 0 |a ENZYME INHIBITORS 
690 1 0 |a GLYCOSIDE HYDROLASES 
690 1 0 |a HYDROLYSIS 
690 1 0 |a MODELS, MOLECULAR 
690 1 0 |a MOLECULAR CONFORMATION 
690 1 0 |a OXIDATION-REDUCTION 
690 1 0 |a PENICILLIUM 
690 1 0 |a PYRROLIDINES 
690 1 0 |a STEREOISOMERISM 
700 1 |a Repetto, E. 
700 1 |a Vega, D.R. 
700 1 |a Varela, O. 
773 0 |d American Chemical Society, 2016  |g v. 81  |h pp. 4179-4189  |k n. 10  |p J. Org. Chem.  |x 00223263  |w (AR-BaUEN)CENRE-337  |t Journal of Organic Chemistry 
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856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00223263_v81_n10_p4179_OliveiraUdry  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v81_n10_p4179_OliveiraUdry  |y Registro en la Biblioteca Digital 
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