Effects of oxygen-sulfur substitution on glycosaminoglycan-priming naphthoxylosides

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 15, 2007, Pages 5283-5299

  Jacobsson, Mårten ^a   Mani, Katrin ^b   Ellervik, Ulf ^a  

^a LUND UNIVERSITY   (Sweden)

^b LUND UNIVERSITY   (Sweden)

Author keywords

Disulfides; Glycosaminoglycan; Thio d xylopyranoside; Thioether; Xylose

Indexed keywords

1 (4 HYDROXYNAPHTHYL) 1 THIO BETA DEXTRO XYLOPYRANOSIDE; 1 (4 O PIVALOYLNAPHTHYL) 1 THIO 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 (4 THIONAPHTHYL) BETA DEXTRO XYLOPYRANOSIDE; 1 (5 HYDROXYNAPHTHYL) 1 THIO BETA DEXTRO XYLOPYRANOSIDE; 1 (5 O PIVALOYLNAPHTHYL) 1 THIO 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 (5 THIONAPHTHYL) BETA DEXTRO XYLOPYRANOSIDE; 1 (8 HYDROXYNAPHTHYL) 1 THIO BETA DEXTRO XYLOPYRANOSIDE; 1 (8 THIONAPHTHYL) BETA DEXTRO XYLOPYRANOSIDE; 1 [3 (PROPYLTHIO)NAPHTH 2 YL] 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 [3 (PROPYLTHIO)NAPHTH 2 YL] BETA DEXTRO XYLOPYRANOSIDE; 1 [4 (PROPYLTHIO)NAPHTH 1 YL] 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 [4 (PROPYLTHIO)NAPHTH 1 YL] BETA DEXTRO XYLOPYRANOSIDE; 1 [5 (PROPYLTHIO)NAPHTH 1 YL] 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 [5 (PROPYLTHIO)NAPHTH 1 YL] BETA DEXTRO XYLOPYRANOSIDE; 1 [6 (PROPYLTHIO)NAPHTH 2 YL] 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 [6 (PROPYLTHIO)NAPHTH 2 YL] BETA DEXTRO XYLOPYRANOSIDE; 1 [7 (PROPYLTHIO)NAPHTH 2 YL] 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 [8 (PROPYLTHIO)NAPHTH 1 YL] 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 1 [8 (PROPYLTHIO)NAPHTH 1 YL] BETA DEXTRO XYLOPYRANOSIDE; 2 (3 HYDROXYNAPHTHYL) 1 THIO BETA DEXTRO XYLOPYRANOSIDE; 2 (3 THIONAPHTHYL) BETA DEXTRO XYLOPYRANOSIDE; 2 (6 HYDROXYNAPHTHYL) 1 THIO BETA DEXTRO XYLOPYRANOSIDE; 2 (6 O PIVALOYLNAPHTHYL) 1 THIO 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 2 (6 THIONAPHTHYL) BETA DEXTRO XYLOPYRANOSIDE; 2 (7 HYDROXYNAPHTHYL) 1 THIO BETA DEXTRO XYLOPYRANOSIDE; 2 (7 O PIVALOYLNAPHTHYL) 1 THIO 2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSIDE; 2 (7 THIONAPHTHYL) BETA DEXTRO XYLOPYRANOSIDE; GLYCOSAMINOGLYCAN; SULFUR DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CELL PROLIFERATION; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; DRUG SYNTHESIS; FETUS; HUMAN; HUMAN CELL; SUBSTITUTION REACTION; TUMOR CELL;

CELL LINE; GLYCOSAMINOGLYCANS; GLYCOSIDES; HUMANS; MOLECULAR STRUCTURE; OXYGEN; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR;

EID: 34249979248     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.008     Document Type: Article

References (41)

1. Schwartz N.B. Trends Glycosci. Glycotechnol. 7 (1995) 429-445
2. Okayama M., Kimata K., and Suzuki S. J. Biochem. 74 (1973) 1069-1073
3. Mani K., Havsmark B., Persson S., Kaneda Y., Yamamoto H., Sakurai K., Ashikari S., Habuchi H., Suzuki S., Kimata K., Malmström A., Westergren-Thorsson G., and Fransson L.-Å. Cancer Res. 58 (1998) 1099-1104
4. Mani K., Belting M., Ellervik U., Falk N., Svensson G., Sandgren S., Cheng F., and Fransson L.-Å. Glycobiology 14 (2004) 387-397
5. Jacobsson M., and Ellervik U. Tetrahedron Lett. 43 (2002) 6549-6552
6. Jacobsson M., Ellervik U., Belting M., and Mani K. J. Med. Chem. 49 (2006) 1932-1938
7. Lehn J.M. Chem. Eur. J. 5 (1999) 2455-2463
8. Ramström O., and Lehn J.-M. ChemBioChem 1 (2000) 41-48
9. Nicolaou K.C., Hughes R., Pfefferkorn J.A., Barluenga S., and Roecker A.J. Chem. Eur. J. 7 (2001) 4280-4295
10. Nilsson U., Johansson R., and Magnusson G. Chem. Eur. J. 2 (1996) 295-302
11. Sobue M., Habuchi H., Ito K., Yonekura H., Oguri K., Sakurai K., Kamohara S., Ueno Y., Noyori R., and Suzuki S. Biochem. J. 241 (1987) 591-601
12. Fritz T.A., Lugemwa F.N., Sarkar A.K., and Esko J.D. J. Biol. Chem. 269 (1994) 300-307
13. Bellamy F., Barberousse V., Martin N., Masson P., Millet J., Samreth S., Sepulchre C., Theveniaux J., and Horton D. Eur. J. Med. Chem. 30 (1995) S101-S115
14. Overman L.E., Smoot J., and Overman J.D. Synthesis 1 (1974) 59-60
15. Humphrey R.E., and Potter J.L. Anal. Chem. 37 (1965) 164-165
16. Amos R.A., and Fawcett S.M. J. Org. Chem. 49 (1984) 2637-2639
17. Stahl C.R., and Siggia S. Anal. Chem. 29 (1957) 154-155
18. Krishnamurthy S., and Aimino D. J. Org. Chem. 54 (1989) 4458-4462
19. Hughes G.K., and Thompson E.O.P. J. Proc. R. Soc. N.S. Wales 82 (1948) 262-264
20. Adams R., and Ferretti A. J. Am. Chem. Soc. 81 (1959) 4939-4940
21. Ferretti A. Organic Syntheses (1973), Wiley & Sons, New York Collect. Vol. 5, 419-421
22. Gleiter R., and Uschmann J. J. Org. Chem. 51 (1986) 370-380
23. Adams R., Reifschneider W., and Ferretti A. Organic Syntheses (1973), Wiley & Sons, New York (Collect. Vol. 5, pp 107-110)
24. Fraser P.K., and Woodward S. Chem. Eur. J. 9 (2003) 776-783
25. Furman F.M., Thelin J.H., Hein D.W., and Hardy W.B. J. Am. Chem. Soc. 82 (1960) 1450-1452
26. Nakazawa T., Hirose N., and Itabashi K. Synthesis (1989) 955-957
27. Charoonniyomporn P., Thongpanchang T., Witayakran S., Thebtaranonth Y., Phillips K.E.S., and Katz T.J. Tetrahedron Lett. 45 (2004) 457-459
28. Ukai S., and Hirose K. Chem. Pharm. Bull. 16 (1968) 606-612
29. Zincke T., and Ruppersberg J. Chem. Ber. 48 (1915) 120-129
30. Rennert H. Chem. Ber. 48 (1915) 459-470
31. Mustafa A., Asker W., Hishmat O.H., Shalaby A.F.A., and Kamel M. J. Am. Chem. Soc. 76 (1954) 5447-5452
32. Zincke T., and Dereser R. Chem. Ber. 51 (1918) 352-360
33. Jusa E., and Breuer G. Monatsh. Chem. 64 (1934) 247-266
34. Lee Y.S., Rho E.S., Min Y.K., Kim B.T., and Kim K.H.J. Carbohydr. Chem. 20 (2001) 503-506
35. Johnsson R., Mani K., and Ellervik U. Bioorg. Med. Chem. 15 (2007) 2868-2877
36. Jacobsson M., Malmberg J., and Ellervik U. Carbohydr. Res. 341 (2006) 1266-1281
37. See for example. Yu H.N., Furukawa J.-i., Ikeda T., and Wong C.-H. Org. Lett. 6 (2004) 723-726
38. Dahmén J., Frejd T., Grönberg G., Magnusson G., and Noori G. Carbohydr. Res. 125 (1984) 161-164
39. Valkó K., Plass M., Bevan C., Reynolds D., and Abraham M.H. J. Chromatogr. A 797 (1998) 41-55
40. Sarkar A.K., Fritz T.A., Taylor W.H., and Esko J.D. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 3323-3327
41. Shively J.E., and Conrad H.E. Biochemistry 15 (1976) 3932-3942