Synthesis and evaluation of two mannosamine-derived lactone-type inhibitors of snail β-mannosidase

Tetrahedron Asymmetry

Volumn 16, Issue 2, 2005, Pages 449-469

  Terinek, Miroslav ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIAMINO 2,5 DIDEOXY DEXTRO GLUCONO 1,5 LACTAM; 2,5 DIAMINO 2,5 DIDEOXY DEXTRO MANNONO 1,5 LACTAM; 5 AMINO 3,4,6 TRI O BENZYL 5 DEOXY 2 O (TRIISOPROPYLSILYL) DEXTRO GLUCONO 1,5 LACTAM; 6,7 BIS(BENZYLOXY) 5 [(BENZYLOXY)METHYL] 5,6,7,8 TETRAHYDROIMIDAZO[1,2 A]PYRIDIN 8 OL; 8 AMINO 5,6,7,8 TETRAHYDRO 5 (HYDROXYMETHYL)IMIDAZO[1,2]PYRIDINE 6,7 DIOL; ALPHA MANNOSIDASE; BETA GLUCOSIDASE; BETA MANNOSIDASE; BETA MANNOSIDASE INHIBITOR; ENZYME INHIBITOR; ETHER DERIVATIVE; IMIDAZOLE DERIVATIVE; LACTAM DERIVATIVE; LACTONE DERIVATIVE; MANNOSAMINE; PYRIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE; SULTONE; TRIISOPROPYLSILYL ETHER; UNCLASSIFIED DRUG;

ALMOND; ARTICLE; CATALYST; CHEMICAL BINDING; ENZYME INHIBITION; HYDROGENATION; ISOMER; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON TRANSPORT; SNAIL; SYNTHESIS;

EID: 12944302096     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.11.068     Document Type: Article

References (61)

1. N. Panday, M. Meyyappan, and A. Vasella Helv. Chim. Acta 83 2000 513
2. V.M.-A. Ducros, D.L. Zechel, G.N. Murshudov, H.J. Gilbert, L. Szabó, D. Stoll, S.G. Withers, and G.J. Davies Angew. Chem., Int. Ed. 41 2002 2824
3. B.V. McCleary Carbohydr. Res. 111 1983 297
4. M.L. Patchett, R.M. Daniel, and H.W. Morgan Biochem. J. 243 1987 779
5. M.P. Dale, H.E. Ensley, K. Kern, K.A.R. Sastry, and L.D. Byers Biochemistry 24 1985 3530
6. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Liskamp, C. Caufield, M. Lipton, G. Chang, T. Hendrickson, and W.C. Still J. Comput. Chem. 11 1990 440
7. T.D. Heightman, A. Vasella, K.E. Tsitsanou, S.E. Zographos, V.T. Skamnaki, and N.G. Oikonomakos Helv. Chim. Acta 81 1998 853
8. T.D. Heightman, and A.T. Vasella Angew. Chem., Int. Ed. 38 1999 750
9. Y. Nishimura, H. Adachi, T. Satoh, E. Shitara, H. Nakamura, F. Kojima, and T. Takeuchi J. Org. Chem. 65 2000 4871
10. M.E. Jung, P.Y.-S. Lam, M.M. Mansuri, and L.M. Speltz J. Org. Chem. 50 1985 1087
11. D. Takada, H. Suemune, and K. Sakai Chem. Pharm. Bull. 38 1990 234
12. T.R. Barbee, and K.F. Albizati J. Org. Chem. 56 1991 6764
13. R.W. Draper, B. Hu, A.T. McPhail, M.S. Puar, E.J. Vater, and L. Weber Tetrahedron 55 1999 3355
14. N.L. Wendler, and D. Taub J. Org. Chem. 25 1960 1828
15. T. Patonay, E. Patonay-Péli, G. Litkei, L. Szilágyi, G. Batta, and Z. Dinya J. Heterocycl. Chem. 25 1988 343
16. T. Konosu, T. Miyaoka, Y. Tajima, and S. Oida Chem. Pharm. Bull. 39 1991 2241
17. M.B. Yunker, and B. Fraser-Reid J. Chem. Soc., Chem. Commun. 1978 325
18. D. Postel, A. Nguyen Van Nhien, and J.L. Marco Eur. J. Org. Chem. 2003 3713
19. G. Opitz Angew. Chem., Int. Ed. Engl. 6 1967 107
20. J.F. King Acc. Chem. Res. 8 1975 10
21. T. Granier, and A. Vasella Helv. Chim. Acta 81 1998 865
22. Granier, T. Dissertation No. 12395, ETH Zürich, 1998
23. R.J.B.H.N. van den Berg, D. Noort, E.S. Milder-Enacache, G.A. van der Marel, J.H. van Boom, and H.P. Benschop Eur. J. Org. Chem. 1999 2593
24. K. Tatsuta, S. Miura, S. Ohta, and H. Gunji Tetrahedron Lett. 36 1995 1085
25. K. Tatsuta, S. Miura, S. Ohta, and H. Gunji J. Antibiot. 48 1995 286
26. O. Mitsunobu Synthesis 1981 1
27. H. Loibner, and E. Zbiral Helv. Chim. Acta 59 1976 2100
28. H. Loibner, and E. Zbiral Helv. Chim. Acta 60 1977 417
29. K. Tatsuta, S. Miura, and H. Gunji Bull. Chem. Soc. Jpn. 70 1997 427
30. M. Jesberger, T.P. Davis, and L. Barner Synthesis 2003 1929
31. T. Granier, N. Panday, and A. Vasella Helv. Chim. Acta 80 1997 979
32. E.J. Corey, and A. Venkateswarlu J. Am. Chem. Soc. 94 1972 6190
33. E.J. Corey, D.H. Hua, B.-C. Pan, and S.P. Seitz J. Am. Chem. Soc. 104 1982 6818
34. Y. Deng, and D.J. Hlasta Tetrahedron Lett. 43 2002 189
35. F. Hammerschmidt, A. Hanninger, B.P. Simov, H. Völlenkle, and A. Werner Eur. J. Org. Chem. 1999 3511
36. J.G. Peters, M. Seppi, R. Fröhlich, B. Wibbeling, and D. Hoppe Synthesis 2002 381
37. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
38. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277
39. M.J. Costanzo, B.E. Maryanoff, L.R. Hecker, M.R. Schott, S.C. Yabut, H.-C. Zhang, P. Andrade-Gordon, J.A. Kauffman, J.M. Lewis, R. Krishnan, and A. Tulinsky J. Med. Chem. 39 1996 3039
40. M. Tao, R. Bihovsky, and J.C. Kauer Bioorg. Med. Chem. Lett. 6 1996 3009
41. K.G. Holden, M.N. Mattson, K.H. Cha, and H. Rapoport J. Org. Chem. 67 2002 5913
42. F.W. Lichtenthaler, M. Lergenmüller, S. Peters, and Z. Varga Tetrahedron: Asymmetry 14 2003 727
43. A.S. Thompson, G.R. Humphrey, A.M. DeMarco, D.J. Mathre, and E.J.J. Grabowski J. Org. Chem. 58 1993 5886
44. N. Panday, T. Granier, and A. Vasella Helv. Chim. Acta 81 1998 475
45. M. Mizuno, and T. Shioiri Chem. Commun. 1997 2165
46. T. Shioiri, and S.-I. Yamada Chem. Pharm. Bull. 22 1974 855
47. N. Panday, and A. Vasella Synthesis 1999 1459
48. M. Terinek, and A. Vasella Helv. Chim. Acta 86 2003 3482
49. M. Terinek, and A. Vasella Helv. Chim. Acta 87 2004 719
50. M. Terinek, and A. Vasella Helv. Chim. Acta. 87 2004 3035
51. Y.T. Li J. Biol. Chem. 242 1967 5474
52. V. Shepherd, and R. Montgomery Biochim. Biophys. Acta 429 1976 884
53. S. Howard, C. Braun, J. McCarter, K.W. Moremen, Y.-F. Liao, and S.G. Withers Biochem. Biophys. Res. Commun. 238 1997 896
54. S. Howard, S. He, and S.G. Withers J. Biol. Chem. 273 1998 2067
55. H.S. Overkleeft, J. van Wiltenburg, and U.K. Pandit Tetrahedron 50 1994 4215
56. J.G. Knight, and K. Tchabanenko Tetrahedron 59 2003 281
57. T. Niwa, T. Tsuruoka, H. Goi, Y. Kodama, J. Itoh, S. Inouye, Y. Yamada, T. Niida, M. Nobe, and Y. Ogawa J. Antibiot. 37 1984 1579
58. G.W.J. Fleet, N.G. Ramsden, and D.R. Witty Tetrahedron 45 1989 319
59. T.K.M. Shing J. Chem. Soc., Chem. Commun. 1988 1221
60. H. Lineweaver, and D. Burk J. Am. Chem. Soc. 56 1934 658
61. I.H. Segel Enzyme Kinetics 1975 Wiley New York