Fluorinated analogues of nojirimycin and mannojirimycin from a non-carbohydrate precursor

Tetrahedron

Volumn 52, Issue 1, 1996, Pages 131-142

  Arnone, Alberto ^a   Bravo, Pierfrancesco ^a   Donadelli, Alessandro ^a   Resnati, Giuseppe ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYNOJIRIMYCIN DERIVATIVE; 1,3,4 TRIDEOXY 3 FLUORONOJIRIMYCIN; GLYCOSIDASE INHIBITOR; ORGANOFLUORINE DERIVATIVE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; ENANTIOMER; FLUORINATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0029655477     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00859-7     Document Type: Article

References (89)

1. Liebig, J.; Wohler, F. Ann. Pharmazie 1837, 21, 96.
2. Springer, T. A. Nature 1990, 346, 425.
3. Stoolman, L. M. Cell 1989, 56, 907.
4. Sharon, N.; Lis, H. Science 1989, 246, 227.
5. Carbohydrate-Protein Interactions; Clarke, A. E.; Wilson, I. A., Eds.; Springer-Verlag: Heidelberg, 1988:
6. Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497.
7. Arends, J.; Willms, B. H. L. Horm. Metab. Res. 1986, 18, 761.
8. Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
9. Nash, R. J.; Fenton, K. A.; Gatehouse, A. M. R.; Bell, E. A. Entomol. Exp. Appl. 1986, 42, 71.
10. Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74.
11. Blough, H. A.; Pauwels, R.; De Clerq, E.; Cogniaux, J.; Sprecher-Goldberger, S.; Thiry, L. Biochem. Biophys. Res. Commun. 1986, 141, 33.
12. Datema, R.; Olafsson, S.; Romero, P. A. Pharmacol. Ther. 1987, 33, 221.
13. Spearman, M. A.; Jamieson, J. C.; Wright, J. A. Expt. Cell. Res. 1987, 168, 116.
14. Tsukamoto, K.; Uno, A.; Shimada, S.; Imokaw, G. Clin. Res. 1989, 37A, 722.
15. Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038.
16. Anzeveno, P. B.; Creemer, L. J.; Daniel, J. K.; King, C.-H. R.; Liu, P. S. J. Org. Chem. 1989, 54, 2539.
17. The piperidine ring of compounds 1-4, 10-13 has been numbered as indicated in the formualas and Schemes. This non-systematic nomenclature has been used as it is commonly adopted for nojirimycin and mannojirimycin analogues (refs. 5). Furthermore, consistency is obtained in numbering systems of acyclic compounds 5-9.
18. Fellows, L. E. Chem Brit. 1987, 842.
19. Fleet, G. W. J. Chem. Brit. 1989, 287.
20. Sinnott, M. L. Chem. Rev. 1990, 90, 1171.
21. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
22. Robinson, K. M.; Rhinehart, B. L.; Ducep, J.-B.; Danzin, C. Drugs Future 1992, 17, 705.
23. Franck, R. W. Bioorg. Chem. 1992, 20, 77.
24. Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
25. (a) Walker, B. D.; Kowalski, M.; Goh, W. C.; Kozarsky, K.; Krieger, M.; Rosen, C.; Rohrschneider, L.; Haseltine, W. A.; Sodroski, I. Proc. Natl. Acad. Sci. USA 1987, 84, 8120.
26. (b) Fleet, G. W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, A. S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Son, J. C.; Wilson, F.; Witty, D. R.; Jacob, G. S.; Rademacher, T.W. FEBS Letters 1988, 237, 128.
27. (c) Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature, 1987, 330, 74.
28. (d) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. USA 1988, 85, 9229.
29. Winkler, D. A.; Holan, G. J. Med. Chem. 1989, 32, 2084.
30. Preliminary communication: Arnone, A.; Bravo, P.; Donadelli A.; Resnati, G. J. Chem. Soc., Chem. Commun. 1993, 984.
31. A detailed mass spectrometric investigation of compounds 3a,b and 4a,b has been performed. It was based on deuterium labelling experiments and mass-analyzed ion kinetic energy spectrometry and allowed the characterization of stereoisomeric 3 and 4: Favretto, D.; Catinella, S.; Traldi, P.; Resnati, G. Rapid Comm. Mass Spectrom. 1994, 8, 653.
32. Murray-Rust, P.; Stallings, W. C.; Monti, C. T.; Preston, K. R.; Glusker, J. P. J. Am. Chem. Soc. 1983, 105, 3206.
33. Takahashi, L. H.; Radhakrishnan, R.; Rosenfield, R. E., Jr.; Meyer, E. F., Jr.; Trainor, D. A. J. Am. Chem. Soc. 1989, 111, 3368.
34. Sunkara, P. S.; Taylor, D. L.; Kang, M. S.; Bowlin, T. L.; Liu, P. S.; Tyms, A. S.; Sjoerdsma, A. Lancet 1989, 1206.
35. Kajimoto, T.; Liu, K. K.-C.; Pederson, R. L.; Zhong, Z.; Ichikawa, J.; Porco, J. A.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6187.
36. Di, J.; Rajanikanth, B.; Szarek, W. J. Chem. Soc., Perkin Trans 1 1992, 2151.
37. Ardron, H.; Butters, T. D.; Platt, F. M.; Wormald, M. R.; Dwek, R. A.; Fleet, G. W. J.; Jacob, G. S. Tetrahedron: Asymmetry 1993, 4, 2011.
38. Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1994, 35, 3143.
39. (a) Fluorinated ketones: Bravo, P.; Piovosi, E.; Resnati, G. J. Chem. Res., (S) 1989, 134,
40. Bravo, P.; Piovosi, E.; Resnati, G. J. Chem. Res., (S) (M) 1989, 1115.
41. (b) Fluorohydrins: Bravo, P.; Ganazzoli, F.; Piovosi, E.; Resnati, G. Gazz. Chim. Ital. 1989, 119, 323.
42. (c) Fluorinated epoxides: Bravo, P.; Frigerio, M.; Resnati, G. Synthesis, 1988, 955.
43. (d) Fluorohydroxy-aldehydes and esters: Bravo, P.; Piovosi, E.; Resnati, G. J. Chem. Soc., Perkin Trans. 1 1989, 1201;
44. Bravo, P.; Pregnolato, M.; Resnati, G. J. Org. Chem. 1992, 57, 2726.
45. (e) Fluorinated tetrahydrofurans, tethahydropyrans, dihydropyrans: Bravo, P.; Ganazzoli, F.; Resnati, G.; Viani, F.; Arnone, A.; Albinati, A. Gazz. Chim. Ital. 1988, 118, 457;
46. Bravo, P.; Resnati, G.; Viani, F.; Arnone, A. J. Chem. Soc., Perkin Trans 1 1989, 839;
47. Arnone, A.; Bravo, P.; Frigerio, M.; Resnati, G.; Viani, F. J. Chem. Res. (S) 1989, 278,
48. Arnone, A.; Bravo, P.; Frigerio, M.; Resnati, G.; Viani, F. J. Chem. Res. (S) (M) 1989, 2201;
49. Arnone, A.; Bravo, P., Resnati, G., Viani, F. J. Chem. Soc., Perkin Trans. 1 1991, 1315.
50. (f) Fluoro substituted nitrogen compounds: Bravo, P.; Resnati, G.; Zappalà, C. J. Fluorine Chem. 1992, 59, 153.
51. (a) Aminocyclopentanols: Arnone A.; Cavicchioli, M.; Donadelli, A.; Resnati, G. Tetrahedron: Asymmetry 1994, 5, 1019.
52. (b) Nucleosides: Bravo, P.; Resnati, G.; Viani, F. Gazz. Chim. Ital. 1992, 122, 493;
53. Bravo, P.; Resnati, G.; Viani, F. Tetrahedron 1993, 49, 713;
54. Bravo, P.; Resnati, G.; Viani, F.; DeMontis, A.; Corrias, S.; La Colla, P. Il Farmaco 1993, 48, 1113.
55. (c) Lactic acid: Bravo, P.; Frigerio, M.; Resnati, G. J. Org. Chem. 1990, 55, 4216.
56. (d) Alkaloids: Bravo, P.; Resnati, G.; Angeli, P.; Frigerio, M.; Viani, F.; Arnone, A.; Marucci, G.; Cantalamessa, F. J. Med. Chem. 1992, 35, 3120.
57. (e) Pyranoses: Bravo, P.; Frigerio, M.; Fronza, G.; Ianni, A.; Resnati, G. Tetrahedron 1990, 46, 997.
58. (f) Furanoses: Bravo, P.; Piovosi, E.; Resnati, G.; Fronza, G. J. Org. Chem. 1989, 54, 5157.
59. Hedhli, A.; Baklouti, A.; Cambon, A. Tetrahedron Lett. 1994, 35, 6877.
60. Reutrakul, V.; Kruahong, T.; Pohmakotr, M. Tetrahedron Lett. 1994, 35, 4851.
61. Reutrakul, V.; Kruahong, T.; Pohmakotr, M. Tetrahedron Lett. 1994, 35, 4853.
62. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707.
63. Matthews, D. P.; Waid, P. P.; Sabol, J. S.; McCarthy, J. R. Tetrahedron Lett. 1994, 35, 5177.
64. Yamazaki, T.; Ishikawa, N.; Iwatsubo, H.; Kitazume, T. J. Chem. Soc., Chem. Commun. 1987, 1340.
65. Robins, M. J.; Wnuk, S. F.; Mullah, K. B.; Dalley, N. K.; Yuan, C.-S.; Lee, Y.; Borchardt, R. T. J. Org. Chem. 1994, 59, 544.
66. McCharthy, J. R.; Jarvi, E. T.; Matthews, D. P.; Edwards, M. L.; Prakash, N. J.; Bowlin, T. L.; Mehdi, S.; Sunkara, P. S.; Bey, P. J. Am. Chem. Soc. 1989, 111, 1127.
67. Herdewijn, P.; De Bruyn, A.; Wigerinck, P.; Hendrix, C.; Kerremans, L.; Rozenski, J.; Busson, R. J. Chem. Soc., Perkin Trans. 1 1994, 249.
68. Bravo, P.; Frigerio, M.; Soloshonok, V.; Viani, F. Tetrahedron Lett. 1993, 34, 7771.
69. Bravo, P.; Capelli, S.; Meille, S. V.; Viani, F.; Zanda, M.; Kukhar, V. P.; Soloshonok. V. A. Tetrahedron: Asymmetry 1994, 5, 2009.
70. Bravo, P.; Mele, A.; Salani, G.; Viani, F. Biorg. Med. Chem. Lett. 1994, 4, 1577.
71. Drabowicz, J.; Bujnicki, B.; Mikolajczyk, M. J. Org. Chem. 1982, 47, 3325.
72. House, H. O.; Lee, L. F. J. Org. Chem. 1976, 41, 863.
73. Bartlett, P. A. in Asymmetric Synthesis, Morrison, J. D., Ed. Academic Press, New York, vol. 3, 1984.
74. Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
75. Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491.
76. Cooper, M. A.; Ward, A. D. Tetrahedron Lett. 1994, 35, 5065.
77. Tamaru, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5731.
78. Takacs, J. M.; Helle, M. A. Tetrahedron Lett. 1989, 30, 7321.
79. Grigg, R.; Hadjisoteriou, M.; Kennewell, P.; Markandu, J.; Thornton-Pett, M. J. Chem. Soc., Chem. Commun. 1992, 1388.
80. Harding, K. E.; Hollingsworth, D. R. Tetrahedron Lett. 1988, 29, 3789.
81. Harding, K. E.; Nam, D. Tetrahedron Lett. 1988, 29, 3793.
82. Liotta, L. J.; Lee, J.; Ganem, B. Tetrahedron 1991, 47, 2433.
83. Hill, L. C.; Whitesides, G. M. J. Am. Chem. Soc. 1974, 96, 870.
84. Clark, L. C., Jr.; Moore, R. E. in: Biomedicinal Aspects of Fluorine Chemistry, Filler, R.; Kobayashi, Y. Eds.; Kodansha Ltd, Tokyo and Elsevier Biomedical Press, Amsterdam; 1982, p. 213.
85. Golden, J. H.; Schreier, C.; Singaram, B.; Williamson, S. M. Inorg. Chem. 1992, 31, 1533.
86. th Winter Fluorine Conference, St. Petersburg, Fl, January 22-27, 1995, P17, 49.
87. Williams, D. R.; Osterhout, M. H.; McGill, J. M. Tetrahedron Lett. 1989, 30, 1327.
88. Perrin, C. L.; Thobum, J. D.; Elsheimer, S. J. Org. Chem. 1991, 56, 7034.
89. Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry. In Methods in Stereochemical Analysis, vol. 4, Marchand, A. P.; Ed.: VCH Publishers, Inc.: Deerfield Beach, Fl, USA, 1985.