C-3- and C-4-alkylated polyhydroxypyrrolidines: Enantiospecific syntheses and glycosidase inhibitory activity

Journal of Organic Chemistry

Volumn 63, Issue 10, 1998, Pages 3411-3416

  Blanco, María Jesús ^a   Sardina, F Javier ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; PYRROLIDINE DERIVATIVE;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IMMUNOREGULATION;

EID: 0032524798     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980078m     Document Type: Article

References (24)

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2. For reviews of glycosidase inhibitors see: (a) Elbein, A. D. Am. Rev. Biochem. 1987, 56, 497. (b) Elbein, A. D. FASEB J. 1991, 5, 3055. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
3. For reviews of glycosidase inhibitors see: (a) Elbein, A. D. Am. Rev. Biochem. 1987, 56, 497. (b) Elbein, A. D. FASEB J. 1991, 5, 3055. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
4. For reviews of glycosidase inhibitors see: (a) Elbein, A. D. Am. Rev. Biochem. 1987, 56, 497. (b) Elbein, A. D. FASEB J. 1991, 5, 3055. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
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12. Only a handful of analogues bearing extra methylene groups have been prepared, Pyrrolidines: (a) Bols, M.; Persson, M. P.; Butt, W. M.; Jørgensen, M.; Christensen, P.; Hansen, L. T. Tetrahedron Lett. 1996, 37, 2097. (b) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
13. Piperidines: (c) Khanna, I. K.; Weier, R. M.; Julien, J.; Mueller, R. A.; Lankin, D. C.; Swenton, L. Tetrahedron Lett. 1996, 37, 1355. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697. (e) Reference 4a. Indolizidines: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 5546.
14. Piperidines: (c) Khanna, I. K.; Weier, R. M.; Julien, J.; Mueller, R. A.; Lankin, D. C.; Swenton, L. Tetrahedron Lett. 1996, 37, 1355. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697. (e) Reference 4a. Indolizidines: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 5546.
15. Piperidines: (c) Khanna, I. K.; Weier, R. M.; Julien, J.; Mueller, R. A.; Lankin, D. C.; Swenton, L. Tetrahedron Lett. 1996, 37, 1355. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697. (e) Reference 4a. Indolizidines: (f) Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 5546.
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19. Molecular Mechanics calculations were carried out with the Accumodel 1.0 program (MicroSimulations). Semiempirical calculations were carried out with the MacSpartan Plus 1.0 program (Wavefunction). Several dozens of starting conformations of each molecule were optimized to find the lowest energy conformer (MM). The structures within 3 kcal of the lowest energy conformers were further optimized by semiempirical (AM1 and PM3) calculations.
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