Synthesis of glucose- and mannose-derived N-acetylamino imidazopyridines and their evaluation as inhibitors of glycosidases

Synthesis

Volumn , Issue SPEC. ISS., 1999, Pages 1459-1468

  Panday, Narendra ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Cyclization; Glycosidase; Imidazoles; Inhibition; N cyanomethylamidine; PK(HA)

Indexed keywords

GLUCOSE; GLYCOSIDASE INHIBITOR; IMIDAZOPYRIDINE DERIVATIVE; MANNOSE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CONFORMATION; CYCLIZATION; ENZYME INHIBITION; MOLECULAR INTERACTION; NONHUMAN;

EID: 0032798741     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3654     Document Type: Article

References (46)

1. T. D. Heightman, M. Locatelli, A. Vasella, Helv. Chim. Acta 1996, 79, 2190.
2. T. D. Heightman, A. Vasella, K. E. Tsitsanou, S. E. Zographos, V. T. Skamnaki, N. G. Oikonomakos, Helv. Chim. Acta 1998, 81, 853.
3. P. Ermert, A. Vasella, Helv. Chim. Acta 1991, 74, 2043.
4. T. Granier, N. Panday, A. Vasella, Helv. Chim. Acta 1997, 80, 979.
5. K. Tatsuta, S. Miura, S. Ohta, H. Gunji, J. Antibiot. 1995, 48, 286.
6. J. Catalan, J. L. M. Abboud, J. Elguero, Adv. Heterocycl. Chem. 1986, 41, 187.
7. K. Schofield, M. R. Grimmett, B. R. T. Keene, 'The Azoles', Cambridge University Press: London, 1976.
8. V. A. Ostrovskii, G. I. Koldobskii, N. P. Shirokiva, V. S. Poplavski, Khim. Geterosikl. Soedin 1981, 581,
9. D. D. Perrin, B. Dempsey, E. P. Serjeant, 'pKa Prediction for Organic Acids and Bases', Chapman and Hall, London, 1981.
10. H. H. Jaffé, H. L. Jones, Adv. Hetrocyclic Chem. 1964, 3, 209.
11. A. R. Katritzky, 'Handbook of Heterocyclic Chemistry', Pergamon: Oxford, 1985.
12. M. Julia, T. Huynh-Dinh, Bull. Soc. Chim. Fr. 1971, 1303.
13. K. Hofman, in 'Chemistry of Heterocyclic Compounds', Ed. A. Weissberger, Interscience: New York, 1953.
14. R. Hoos, A. B. Naughton, A. Vasella, Helv. Chim. Acta 1993, 76, 1802.
15. H. S. Overkleeft, J. van Wiltenburg, U. K. Pandit, Tetrahedron 1994, 50, 4215.
16. H. Bader, J. D. Downer, P. Driver, J. Chem. Soc. 1950, 2775.
17. H. Bader, J. D. Downer, J. Chem. Soc. 1953, 1636.
18. J. Heyes, N. Ward, Chem. Abstr. 1972, 77, 19645a.
19. A. McKillop, A. Henderson, P. S. Ray, C. Avendaño, E. G. Molinero, Tetrahedron Lett. 1982, 23, 3357.
20. E. Gomez, C. Avendaño, A. McKillop, Tetrahedron 1986, 42, 2625.
21. K. T. Potts, S. Husain, J. Org. Chem. 1971, 36, 3368.
22. A. Chinone, S. Sato, M. Ohta, Bull. Chem. Soc. Jpn. 1971, 44, 826.
23. R. Hoos, A. B. Naughton, W. Thiel, A. Vasella, W. Weber, K. Rupitz, S. G. Withers, Helv. Chim. Acta 1993, 76, 2666.
24. G. Papandreou, M. K. Tong, B. Ganem, J. Am. Chem. Soc 1993, 115, 11682.
25. H. U. Sieveking, W. Lüttke, Liebigs Ann. Chem. 1977, 2, 189.
26. G. Legler, M.-T. Finken, Carbohydr. Res. 1996, 292, 103.
27. T. Granier, F. Gaiser, L. Hintermann, A. Vasella, Helv. Chim. Acta 1997, 80, 1443.
28. N. Panday, T. Granier, A. Vasella, Helv. Chim. Acta 1998, 81, 475.
29. P. Fowler, B. Bernet, A. Vasella, Helv. Chim. Acta 1996, 79, 269.
30. M. Avalos, R. Babiano, C. J. Duran, J. L. Jimenez, J. C. Palacios, J. Chem. Soc. Perkin Trans. 2 1992, 2, 2205-2215.
31. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 400.
32. R. Hoos, A. Vasella, K. Rupitz, S. G. Withers, Carbohydr. Res. 1997, 298, 291.
33. H. Lineweaver, D. Burk, J. Am. Chem. Soc. 1934, 56, 658.
34. I. H. Segel, 'Enzyme Kinetics', Wiley: New York, 1975.
35. HA of 6 and the one of 1-methylimidazole.
36. The positions 4 and 5 of imidazoles correspond to the positions 2 and 3 of pyridoazoles.
37. 21,22
38. -1).
39. In view of the endocyclic double bond of the amindine, we expected alkylation of the endocyclic rather than the exocyclic nitrogen. This was confirmed later by comparison of the 2-acetamidoimidazoles 22 and 24 with the 3-acetamidoimidazoles 29 and 30.
40. There was no TLC evidence for the N-cyanomethylamidine 1 s 19 and 20.
41. 6.
42. The data in reference 4 are those of the protonated 6.
43. 2O.
44. 29,30
45. HA of 11.
46. Prepared from aminoacetonitrile hydrochloride according to reference 12.