Approaches to carbocyclic sialidase inhibitors

Monatshefte fur Chemie

Volumn 133, Issue 10, 2002, Pages 1263-1278

  Streicher, Hansjörg ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Carbocycles; Influenza virus neuraminidase; Sialidase; Sialidase inhibitors

Indexed keywords

EID: 57249105075     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-002-0503-x     Document Type: Review

References (69)

1. Angata T, Varki A (2002) Chem Rev 102: 439
2. Schauer R, Kamerling JP (1997) Chemistry, biochemistry and biology of sialic acids. In: Montreuil J, Vliegenhardt JFG, Schachter H (eds) Glycoproteins II. Elsevier, Amsterdam, p 243
3. Schauer R (2000) Biochemistry of sialic acid diversity. In: Ernst B, Hart GW, Sinay P (eds) Carbohydrates in Chemistry and Biology. Wiley-VCH, Weinheim, p 227
4. Schauer R (2000) Glycoconj J 17: 485
5. Traving C, Schauer R (1998) Cell Mol Life Sci 54: 1330
6. Vimr ER (1994) Trends in Microbiol 2: 271
7. Corfield T (1992) Glycobiology 2: 509
8. Roberts NA (2001) Prog Drug Res 56: 195
9. Dyason JC, von Itzstein M (2001) Aust J Chem 54: 663
10. Gubareva LV, Kaiser L, Hayden FG (2000) Lancet 355: 827
11. Meindl P, Tuppy H (1969) Monatsh Chem 100: 1295
12. von Itzstein M, Wu W, Kok GB, Pegg MS, Dyason JC, Jin B, Phan T, Smythe ML, White HF, Oliver SW, Colman PM, Varghese JN, Ryan DM, Woods JM, Bethell RC, Hotham VJ, Cameron JM, Penn CR (1993) Nature 363: 418
13. von Itzstein M, Dyason JC, Oliver SW, White HF, Wu W, Kok GB, Pegg MS (1996) J Med Chem 39: 388
14. Kiefel MJ, von Itzstein M (2002) Chem Rev 102: 471
15. Kim CU, Lew W, Williams MA, Liu H, Zhang L, Swaminathan S, Bischofberger N, Chen MS, Mendel DB, Tai CY, Laver WG, Stevens RC (1997) J Am Chem Soc 119: 681
16. Kim CU, Lew W, Williams MA, Zhang L, Chen X, Escarpe PA, Mendel DB, Laver WG, Stevens RC (1998) J Med Chem 41: 2451
17. Luo M, Jedrzejas MJ, Singh S, White CL, Brouilette WJ, Air GM, Laver WG (1995) Acta Cryst D51: 504
18. Singh S, Jedrzejas MJ, Air GM, Luo M, Laver WG, Brouilette WJ (1995) J Med Chem 38: 3217
19. Jedrzejas MJ, Singh S, Brouilette WJ, Laver WG, Air GM, Luo M (1995) Biochemistry 34: 3144
20. Chand P, Babu YS, Bantia S, Chu N, Cole LB, Kotian PL, Laver WG, Montgomery JA, Pathak VP, Petty SL, Shrout DP, Walsh DA, Walsh GM (1997) J Med Chem 40: 4030
21. Williams M, Bischofberger N, Swaminathan S, Kim CU (1995) Bioorg Med Chem Lett 5: 2251
22. Sudbeck EA, Jedrzejas MJ, Singh S, Brouilette WJ, Air GM, Laver WG, Babu YS, Bantia S, Chand P, Chu N, Montgomery JA, Walsh DA, Luo M (1997) J Mol Biol 267: 584
23. Brouillette WJ, Atigadda VR, Luo M, Air GM, Babu YS, Bantia S (1999) Bioorg Med Chem Lett 9: 1901
24. Atigadda VR, Brouilette WJ, Duarte F, Ali SM, Babu YS, Bantia S, Chand P, Chu N, Montgomery JA, Walsh DA, Sudbeck EA, Finley J, Luo M, Air GM, Laver WG (1999) J Med Chem 42: 2332
25. Finley JB, Atigadda VR, Duarte F, Zhao JJ, Brouilette WJ, Air GM, Laver WG (1999) J Mol Biol 293: 1107
26. Burmeister WP, Ruigrok RW, Cusack S (1992) EMBO J 11: 49
27. Varghese JN, McKimm-Breschkin JL, Caldwell JB, Kortt AA, Colman PM (1992) Proteins 14: 327
28. Bossart-Whitaker P, Carson M, Babu YS, Smith CD, Laver WG, Air GM (1993) J Mol Biol 232: 1069
29. Burmeister WP, Henrissat P, Bosso C, Cusack S, Ruigrok RW (1993) Structure 1: 19
30. Bianco A, Brufani M, Melchioni C (2001) Farmaco 56: 305
31. Engstler M, Ferrero-Garcia MA, Parodi AJ, Schauer R, Storz-Eckerlin T, Vasella A, Witzig C, Zhu X (1994) Helv Chim Acta 77: 1166
32. Edmond JD, Johnston RG, Kidd D, Rylance HJ, Sommerville RG (1966) Br J Pharmac Chamother 27: 415
33. Brossmer R, Keilich G, Ziegler D (1977) Hoppe Seyler's Z Physiol Chem 358: 391
34. Vasella A, Wyler R (1990) Helv Chim Acta 73: 1742
35. Mack H, Brossmer R (1987) Tetrahedron Lett 28: 191
36. Chandler M, Conroy R, Cooper AWJ, Lamont RB, Scicinski JJ, Smart JE, Storer R, Weir NG, Wilson RD, Wyatt PG (1955) J Chem Soc Perkin Trans I, 1189
37. Rohloff JC, Kent KM, Postich MJ, Becker MW, Chapman HH, Kelly DE, Lew W, Louie MS, McGee LR, Prisbe EJ, Schultze LM, Yu RH, Zhang L (1998) J Org Chem 63: 4545
38. Karpf M, Trussardi R (2001) J Org Chem 66: 2044
39. Bianco A, Brufani M, Manna F, Melchioni C (2001) Carb Res 332: 23
40. Lew W, Wu H, Mendel DB, Escarpe PA, Chen X, Laver GW, Graves BJ, Kim CU (1998) Bioorg Med Chem Lett 8: 3321
41. Lew W, Wu H, Chen X, Graves BJ, Escarpe PA, MacArthur HL, Mendel DB, Kim CU (2000) Bioorg Med Chem Lett 10: 1257
42. Vorwerk S, Vasella A (1998) Angew Chem 110: 1765
43. Kerrigan SA, Smith PW, Stoodley RJ (2001) Tetrahedron Lett 42: 4709
44. Kerrigan SA, Pritchard RG, Smith PW, Stoodley RJ (2001) Tetrahedron Lett 42: 7687
45. Wallimann K, Vasella A (1990) Helv Chim Acta 73: 1359
46. Streicher H, Meisch J, Bohner C (2001) Tetrahedron 57: 8851
47. Parr IB, Horenstein BA (1997) J Org Chem 62: 7489
48. Fleet GWJ, Shing TKM, Warr SM (1984) J Chem Soc Perkin Trans I, 905
49. Mirza S, Vasella A (1984) Helv Chim Acta 67: 1562
50. Mirza S, Harvey J (1991) Tetrahedron Lett 32: 4111
51. Streicher H, Bohner M (2002) Tetrahedron (in press)
52. Hochgürtel M, Kroth H, Piecha D, Hofmann MW, Nicolau C, Krause S, Schaaf O, Sonnenmoser G, Eliseev AV (2002) Proc Natl Acad Sci USA 99: 3382
53. Hasenknopf B, Lehn JM, Kneisel BO, Baum G, Fenske D (1996) Angew Chem Int Ed Engl 35: 1838
54. Ogawa S, Yoshikawa M, Taki T, Yokoi S, Chida N (1995) Carb Res 269: 53
55. Baumberger F, Vasella A, Schauer R (1988) Helv Chim Acta 71: 429
56. Yamamoto T, Kumazawa H, Inami K, Teshima T, Shiba T (1992) Tetrahedron Lett 33: 5791
57. Wang GT, Chen Y, Wang S, Gentles R, Sowin T, Kati W, Muchmore S, Giranda V, Stewart K, Sham H, Kempf D, Laver WG (2001) J Med Chem 44: 1192
58. Babu YS, Chand P, Bantia S, Kotian P, Dehghani A, El Kattan Y, Lin TH, Hutchison TL, Elliott AJ, Parker CD, Ananth SL, Horn LL, Laver WG, Montgomery JA (2000) J Med Chem 43: 3482
59. Bantia S, Parker CD, Ananth SL, Horn LL, Andries K, Chand P, Kotian PL, Dehghani A, El Kattan Y, Lin T, Hutchison TL, Montgomery JA, Kellog DL, Babu YS (2001) Antimicrob Agents Chemother 45: 1162
60. Korytnyk W, Angelino N, Klohs W, Bernacki R (1980) Eur J Med Chem 15: 77
61. Müller B, Schaub C, Schmidt RR (1998) Angew Chem Int Ed Engl 37: 2893
62. Schaub C, Müller B, Schmidt RR (2000) Eur J Org Chem 1745
63. Compain P, Martin OR (2001) Bioorg Med Chem 9: 3077
64. Klohs WD, Bernacki RJ, Korytnyk W (1979) Cancer Res 39: 1231
65. Thoma G, Kinzy W, Bruns C, Patton JT, Magnani JL, Thoma G (1999) J Med Chem 42: 4909
66. Bänteli R, Ernst B (2001) Bioorg Med Chem Lett 11: 459
67. Sears P, Wong CH (1999) Angew Chem Int Ed Engl 38: 2300
68. Roy R (1997) In: Witczak ZJ, Nieforth KA (eds) Carbohydrates in Drug Design. Dekker, New York, p 83
69. Simanek EE, McGarvey GJ, Jablonowski JA, Wong CH (1998) Chem Rev 98: 833