Polycyclitols - Novel conduritol and carbasugar hybrids as new glycosidase inhibitors

Canadian Journal of Chemistry

Volumn 83, Issue 6-7, 2005, Pages 581-594

  Mehta, Goverdhan ^a   Ramesh, Senaiar S ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Carbasugar; Conduritol; Glycomimics; Glycosidase inhibitors

Indexed keywords

REACTION KINETICS; SYNTHESIS (CHEMICAL);

GLYCOSIDASE; POLYCYCLITOLS;

AROMATIC HYDROCARBONS;

1,3 CYCLOHEXADIENE DERIVATIVE; 1,4 BENZOQUINONE; 5,5 DIMETHOXY 1,2,3,4 TETRACHLOROCYCLOPENTADIENE; 7 KETONORBORNENONE; ALPHA GLUCOSIDASE; BICYCLITOL; BICYCLO COMPOUND; CARBASUGAR; CARBOHYDRATE; CARBON MONOXIDE; CONDURITOL AZIRIDINE; CYCLOPENTADIENE DERIVATIVE; DECALIN; FUNCTIONAL GROUP; GLYCOSIDASE INHIBITOR; HYDRINDANE; INDAN DERIVATIVE; NORBORNENE DERIVATIVE; POLYCYCLITOL DERIVATIVE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; ELIMINATION REACTION; ENZYME INHIBITION; HEAT TREATMENT; HYDROXYLATION; MOLECULAR MIMICRY; POLYMERIZATION; REGIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 29244469393     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-032     Document Type: Article

References (61)

1. Recent reviews: (a) N. Asano. Glycobiology, 13, 93R (2003);
2. (b) C.-H. Wong. Acc. Chem. Res. 32, 376 (1999);
3. (c) T.D. Heightman and A.T. Vasella. Angew. Chem. Int. Ed. 38, 750 (1999);
4. (d) P. Sears and C.-H. Wong. Angew. Chem. Int. Ed. 38, 2300 (1999);
5. (e) M. Bols. Acc. Chem. Res. 31, 1 (1998);
6. (f) S. Ogawa. In Carbohydrate mimics: Concepts and methods. Edited by Y. Chapleur. Wiley-VCH, Weinheim. 1998. p. 87;
7. (g) B. Ganem. Acc. Chem. Res. 29, 340 (1996);
8. (h) S.G. Withers. Pure Appl. Chem. 67, 1673 (1995);
9. (i) G.S. Jacob. Curr. Opin. Struct. Biol. 5, 605 (1995);
10. (j) A.D. Albein. Annu. Rev. Biochem. 56, 497 (1987).
11. (a) A. Berecibar, C. Grandjean, and A. Siriwardena. Chem. Rev. 99, 779 (1999);
12. (b) C.R. Johnson. Acc. Chem. Res. 31, 333 (1998);
13. (c) A. Martinez-Grau and J. Marco-Contelles. Chem. Soc. Rev. 27, 155 (1998);
14. (d) Y. Landais. Chimia, 52, 104 (1998);
15. (e) T. Hudlicky, D.A. Entwistle, K.K. Pitzer, and A.J. Thorpe. Chem. Rev. 96, 1195 (1996);
16. (f) R.J. Ferrier and S. Middleton. Chem. Rev. 93, 2779 (1993);
17. (g) T. Suami. Top. Curr. Chem. 154, 257 (1990).
18. (a) M.S. Gultekin, M. Celik, and M. Balci. Curr. Org. Chem. 8, 1159 (2004);
19. (b) M. Balci. Pure Appl. Chem. 69, 97 (1997);
20. (c) T. Hudlicky and J.W. Reed. In Advances in asymmetric synthesis. Vol. 1. JAI Press, Greenwich. 1995. p. 271;
21. (d) T. Hudlicky and M. Cebulak. In Cyclitols and their derivatives. A handbook of physical, spectral and synthetic data. Wiley-VCH, New York. 1993;
22. (e) H.A.J. Carless. Tetrahedron: Asymmetry, 3, 795 (1992);
23. (f) M. Balci, Y. Sutbeyaz, and H. Secen. Tetrahedron, 46, 3715 (1990).
24. (a) M. Desjardins, M.-C. Lallemand, S. Freeman, T. Hudlicky, and K.A. Abboud. J. Chem. Soc. Perkin Trans, 1, 621 (1999);
25. (b) Y. Kara, M. Balci, S.A. Bourne, and W.H. Watson. Tetrahedron Lett. 35, 3349 (1994).
26. (a) N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet. Tetrahedron: Asymmetry, 11, 1645 (2000);
27. (b) A.E. Stütz. In Iminosugars as glycosidase inhibitors: Nojirimycin and beyond. Wiley-VCH, Weinheim. 1999;
28. (c) J. Michael. Nat. Prod. Rep. 16, 675 (1999);
29. (d) A. de Raadt, C.W. Ekhart, M. Ebner, and A.E. Stütz. Top. Curr. Chem. 187, 157 (1997);
30. (e) B. Ganem. Acc. Chem. Res. 29, 340 (1996);
31. (f) G.W.J. Fleet and B. Winchester. Glycobiology, 2, 199 (1992);
32. (g) P.S. Liu, R.S. Rogers, M.S. Kang, and P.S. Sunkara. Tetrahedron Lett. 32, 5853 (1991).
33. (h) M.L. Sinnot. Chem. Rev. 90, 1171 (1990);
34. (i) G. Legler. Adv. Carbohydr. Chem. Biochem. 48, 319 (1990).
35. The work described has already been published as preliminary communications.
36. (a) G. Mehta and S.S. Ramesh. Tetrahedron Lett. 42, 1987 (2001);
37. (b) G. Mehta and S.S. Ramesh. Chem. Commun. 2429 (2000).
38. (a) G. Mehta and D.S. Reddy. Tetrahedron Lett. 40, 9137 (1999);
39. (b) G. Mehta, D.S. Reddy, S.S. Ramesh, and U. Tatu. Tetrahedron Lett. 40, 9141 (1999).
40. (a) D.S. Reddy. Ph.D. dissertation, University of Hyderabad, Hyderabad, India. 2000;
41. (b) CA. Peri. Gazz. Chim. Ital. 85, 1118 (1995).
42. S. Takano, M. Moriya, K. Tanaka, and K. Ogasawara. Synthesis, 687 (1994).
43. (a) M. Schröder. Chem. Rev. 80, 187 (1980).
44. (b) V. VanRheenen, R.C. Kelly, and D.Y. Cha. Tetrahedron Lett. 17, 1973 (1976).
45. (a) E.T. McBee, W.R. Diveley, and J.E. Burch. J. Am. Chem. Soc. 77, 385 (1955);
46. (b) F.H. Allen. Chem. Rev. 45, 309 (1945).
47. P.F. Schuda, H.L. Ammon, M.R. Heimann, and S. Battacharjee. J. Org. Chem. 47, 3434 (1982).
48. (a) R. Uma. Ph.D. dissertation, University of Hyderabad, Hyderabad, India. 1999;
49. (b) M. Balci. Chem. Rev. 81, 91 (1981);
50. R.W. Denny and A. Nickon. In Organic reactions. Vol. 20. John Wiley and Sons, New York. 1973. p. 133.
51. (a) J.K. Cha, W.J. Christ, and Y. Kishi. Tetrahedron Lett. 37, 3943 (1983);
52. (b) W.J. Christ, J.K. Cha, and Y. Kishi. Tetrahedron Lett. 37, 3947 (1983).
53. A.P. Marchand and T.-C. Chou. J. Chem. Soc. Perkin Trans, 1, 1948 (1973).
54. (a) A.P. Marchand, W.D. La Roe, G.V.M. Sharma, C.S. Suresh, and D.S. Reddy. J. Org. Chem. 51, 1622 (1986);
55. (b) T.-C. Chou and J.H. Chiou. J. Chin. Chem. Soc. (Taipei), 33, 227 (1986).
56. J.-L. Luche. J. Am. Chem. Soc. 100, 2226 (1978).
57. (a) K. Sugahara and I. Yamashina. In Methods in enzymology. Edited by C. Ginsburg. Vol. XXVIII. Part B. Academic Press, New York. 1972. p. 769;
58. (b) A.L. Tarentino and F. Maley. In Methods in enzymology. Edited by C. Ginsburg. Vol. XXVIII. Part B. Academic Press, New York. 1972. p. 772;
59. (c) O.P. Bail and K.M.L. Agrawal. J. Biochem. Chem. 244, 2970 (1969);
60. (d) Y-T. Li. J. Biochem. Chem. 242, 5474 (1969);
61. (e) H. Lineweaver and D. Burk. J. Am. Chem. Soc. 56, 658 (1934).