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 |
Referencias:
- D'Alessio, C., Dahms, N.M., (2015) Curr. Protein Pept. Sci., 16, pp. 31-48
- Jacobs, P.P., Callewaert, N., (2009) Curr. Mol. Med., 9, pp. 774-800
- Kato, K., Kamiya, Y., (2007) Glycobiology, 17, pp. 1031-1044
- Sjögren, J., Collin, M., (2014) Future Microbiol., 9, pp. 1039-1051
- Gorelik, E., Galili, U., Raz, A., (2001) Cancer Metastasis Rev., 20, pp. 245-277
- Gerber-Lemaire, S., Juillerat-Jeanneret, L., (2006) Mini-Rev. Med. Chem., 6, pp. 1043-1052
- Asano, N., (2009) Cell. Mol. Life Sci., 66, pp. 1479-1492
- Kajimoto, T., Node, M., (2009) Curr. Top. Med. Chem., 9, pp. 13-33
- Moorthy, N.S.H.N., Ramos, M.J., Fernandes, P.A., (2012) Mini-Rev. Med. Chem., 12, pp. 713-720
- Wang, J.-T., Lin, T.-C., Chen, Y.-H., Lin, C.-H., Fang, J.-M., (2013) MedChemComm, 4, pp. 783-791
- Horne, G., Wilson, F.X., Tinsley, J., Williams, D.H., Storer, R., (2011) Drug Discovery Today, 16, pp. 107-118
- Stütz, A.E., (1999) Iminosugars As Glycosidase Inhibitors, , Ed. Wiley-VCH: Weinheim
- Scott, L.J., Spencer, C.M., (2000) Drugs, 59, pp. 521-549
- Winchester, B., (2006) The Development of Iminosugars As Drugs in Glycobiology, pp. 308-324. , Sansom, C. Markman, O. Scion Publishing Ltd: Bloxham
- Zitzmann, N., Block, T., Methta, A., Rudd, P., Burton, D., Wilson, I., Platt, F., Dwek, R.A., (2005) Adv. Exp. Med. Biol., 564, pp. 1-2
- Butters, T.D., Dwek, R.A., Platt, F.M., (2005) Glycobiology, 15, pp. 43R-52R
- Cox, T.M., (2005) Acta Paediatr., 94, pp. 69-75
- Durantel, D., (2009) Curr. Opin. Invest. Drugs, 10, pp. 860-870
- Fish, P.V., Andrews, M.D., Fray, M.J., Stobie, A., Wakenhut, F., Whitlock, G.A., (2009) Bioorg. Med. Chem. Lett., 19, pp. 2829-2834
- Winchester, B.G., (2009) Tetrahedron: Asymmetry, 20, pp. 645-651
- Vasella, A., Davies, G.J., Böhm, M., (2002) Curr. Opin. Chem. Biol., 6, pp. 619-629
- Trost, B.M., Horne, D.B., Woltering, M.J., (2006) Chem. - Eur. J., 12, pp. 6607-6620
- Sinnott, M.L., (1990) Chem. Rev., 90, pp. 1171-1202
- Legler, G., (1990) Adv. Carbohydr. Chem. Biochem., 48, pp. 319-384
- Stütz, A.E., (1996) Angew. Chem., Int. Ed. Engl., 35, pp. 1926-1928
- Heightman, T.D., Vasella, A.T., (1999) Angew. Chem., Int. Ed., 38, pp. 750-770
- Lillelund, V.H., Jensen, H.H., Liang, X., Bols, M., (2002) Chem. Rev., 102, pp. 515-553
- Asano, N., Nash, R.J., Molyneux, R.J., Fleet, G.W.J., (2000) Tetrahedron: Asymmetry, 11, pp. 1645-1680
- Molyneux, R.J., Pan, Y.T., Tropea, J.E., Elbein, A.D., Lawyer, C.H., Hughes, D.J., Fleet, G.W.J., (1993) J. Nat. Prod., 56, pp. 1356-1364
- Nash, R.J., Asano, N., Watson, A.A., (1996) Alkaloids: Chemical and Biological Perspectives, 2, pp. 345-376. , Pelletier, S. W. Elsevier Science: Oxford
- Watson, A.A., Nash, R.J., Wormald, M.R., Harvey, D.J., Dealler, S., Lees, E., Asano, N., Fleet, G.W.J., (1997) Phytochemistry, 46, pp. 255-259
- Asano, N., Kato, A., Miyauchi, M., Kizu, H., Kameda, Y., Watson, A.A., Nash, R.J., Fleet, G.W.J., (1998) J. Nat. Prod., 61, pp. 625-628
- Kato, A., Adachi, I., Miyauchi, M., Ikeda, K., Komae, T., Kizu, H., Kameda, Y., Asano, N., (1999) Carbohydr. Res., 316, pp. 95-103
- Compain, P., Chagnault, V., Martin, O.R., (2009) Tetrahedron: Asymmetry, 20, pp. 672-711
- Stocker, B.L., Dangerfield, E.M., Win-Mason, A.L., Haslett, G.W., Timmer, M.S.M., (2010) Eur. J. Org. Chem., pp. 1615-1637
- Doddi, V.R., Vankar, Y.D., (2007) Eur. J. Org. Chem., pp. 5583-5589
- Rodriguez-Borges, J.E., Vale, M.L.C., Rizzo Aguiar, F., Alves, M.J., García-Mera, X., (2008) Synthesis, 2008, pp. 971-977
- Petakamsetty, R., Jain, V.K., Majhi, P.K., Ramapanicker, R., (2015) Org. Biomol. Chem., 13, pp. 8512-8523
- Lo Fiego, M.J., Marino, C., Varela, O., (2015) RSC Adv., 5, pp. 45631-45640
- Repetto, E., Marino, C., Varela, O., (2013) Bioorg. Med. Chem., 21, pp. 3327-3333
- Repetto, E., Manzano, V.M., Uhrig, M.L., Varela, O., (2012) J. Org. Chem., 77, pp. 253-265. , references cited therein
- Udry, G.A.O., Repetto, E., Varela, O., (2014) J. Org. Chem., 79, pp. 4992-5006
- Richards, M.R., Lowary, T.L., (2009) ChemBioChem, 10, pp. 1920-1938
- Peltier, P., Euzen, R., Daniellou, R., Nugier-Chauvin, C., Ferrières, V., (2008) Carbohydr. Res., 343, pp. 1897-1923
- Miletti, L.C., Marino, K., Marino, C., Colli, W., Alves, M.J.M., Lederkremer, R.M., (2003) Mol. Biochem. Parasitol., 127, pp. 85-88
- Wallis, G.L.F., Hemming, F.W., Peberdy, J.F., (2001) Biochim. Biophys. Acta, Gen. Subj., 1525, pp. 19-28
- Kissane, M., Maguire, A.R., (2010) Chem. Soc. Rev., 39, pp. 845-883
- Adrio, J., Carretero, J.C., (2014) Chem. Commun., 50, pp. 12434-12446
- Narayan, R., Potowski, M., Jia, Z., Antonchick, A.P., Waldmann, H., (2014) Acc. Chem. Res., 47, pp. 1296-1310
- Hashimoto, T., Maruoka, K., (2015) Chem. Rev., 115, pp. 5366-5412
- Singh, M.S., Chowdhury, S., Koley, S., (2016) Tetrahedron, 72, pp. 1603-1644
- Iriarte Capaccio, C.A., Varela, O., (2001) J. Org. Chem., 66, pp. 8859-8866
- Iriarte Capaccio, C.A., Varela, O., (2002) J. Org. Chem., 67, pp. 7839-7846
- Iriarte Capaccio, C.A., Varela, O., (2003) Tetrahedron Lett., 44, pp. 4023-4026
- Cagnoni, A.J., Uhrig, M.L., Varela, O., (2009) Bioorg. Med. Chem., 17, pp. 6203-6212
- Colomer, J.P., Manzano, V.E., Varela, O., (2013) Eur. J. Org. Chem., 2013, pp. 7343-7353
- Sousa, C.A.D., Rizzo-Aguiar, F., Vale, M.L.C., García-Mera, X., Caamano, O., Rodríguez-Borges, J.E., (2012) Tetrahedron Lett., 53, pp. 1029-1032
- Deetz, M.J., Jonas, M., Malerich, J.P., Smith, B.D., (2002) Supramol. Chem., 14, pp. 487-489
- Bleich, H., Wilde, J., (1984) J. Magn. Reson., 56, pp. 149-150
- Hennig, J., Limbach, H.H., (1982) J. Magn. Reson., 49, pp. 322-328
- Davis, D.G., Bax, A., (1985) J. Magn. Reson., 64, pp. 533-535
- Rietschel-Berst, M., Jentoft, N.H., Rick, P.D., Pletcher, C., Fang, F., Gander, J.E., (1977) J. Biol. Chem., 252, pp. 3219-3226
- Marino, C., Marino, K., Miletti, L., Manso Alves, M.J., Colli, W., De Lederkremer, R.M., (1998) Glycobiology, 8, pp. 901-904
- Marino, C., Baldoni, L., (2014) ChemBioChem, 15, pp. 188-204
- Imamura, A., Lowary, T., (2011) Trends Glycosci. Glycotechnol., 23, pp. 134-152
- Bordoni, A., De Lederkremer, R.M., Marino, C., (2010) Bioorg. Med. Chem., 18, pp. 5339-5345
- Sarotti, A.M., Spanevello, R.A., Suárez, A.G., Echeverría, G.A., Piro, O.E., (2012) Org. Lett., 14, pp. 2556-2559
- Brazier, J.B., Tomkinson, N.C.O., (2010) Top. Curr. Chem., 291, pp. 281-347
- Mukherjee, S., Yang, J.W., Hoffmann, S., List, B., (2007) Chem. Rev., 107, pp. 5471-5569
- Sulzer-Mossé, S., Alexakis, A., (2007) Chem. Commun., pp. 3123-3135
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