Rebeccamycin analogues bearing amine substituents or other groups on the sugar moiety

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 17, 2003, Pages 3709-3722

  Anizon, Fabrice ^a   Moreau, Pascale ^a   Sancelme, Martine ^a   Laine, William ^b   Bailly, Christian ^b   Prudhomme, Michelle ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

12 (3 AMINO 3 DEOXY 4 O METHYL BETA DEXTRO ALTROPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 (5,6 ANHYDRO 4 O METHYL BETA DEXTRO GLUCOPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 (6 AMINO 6 DEOXY 4 O METHYL BETA DEXTRO GLUCOPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 (6 AZIDO 6 DEOXY 4 O METHYL BETA DEXTRO GLUCOPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 (6 CHLORO 6 DEOXY 4 O METHYL BETA DEXTRO GLUCOPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 C]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 (6 DEOXY 4 O METHYL BETA DEXTRO 6 METHYLAMINOGLUCOPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 (6 DEOXY 6 DIMETHYLAMINO 4 O METHYL BETA DEXTRO GLUCOPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 (6 DEOXY 6 IODO 4 O METHYL BETA DEXTRO GLUCOPYRANOSYL) 6,7,12,13 TETRAHYDRO (5H) INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; 12 [6 (3 AZABICYCLO[3.3.0]OCTYL) 4 O METHYL BETA DEXTRO GLUCOPYRANOSYL] 6,7,12,13 TETRAHYDROINDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7 DIONE; AMINE; AMINO ACID DERIVATIVE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); REBECCAMYCIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACILLUS CEREUS; CANDIDA ALBICANS; CONTROLLED STUDY; DNA CLEAVAGE; DRUG DNA BINDING; DRUG SOLUBILITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MOLECULAR INTERACTION; NONHUMAN; STREPTOMYCES CHARTREUSIS; STRUCTURE ACTIVITY RELATION; YEAST;

BACILLUS CEREUS; BACTERIA (MICROORGANISMS); CANDIDA; CANDIDA ALBICANS; ESCHERICHIA COLI; NEGIBACTERIA; POSIBACTERIA; STREPTOMYCES; STREPTOMYCES CHARTREUSIS;

EID: 0042121548     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00343-2     Document Type: Article

References (33)

1. Prudhomme M. Curr. Pharm. Des. 3:1997;265.
2. Pindur U., Kim Y.-S., Mehrabani F. Curr. Med. Chem. 6:1999;29.
3. Long B.H., Balasubramanian B.N. Exp. Opin. Ther. Pat. 10:2000;635.
4. Long B.H., Rose W.C., Vyas D.M., Matson J.A., Forenza S. Curr. Med. Chem. Anti-Cancer Agents. 2:2002;255.
5. Ruegg U.T., Burgess G.M. Trends Pharmacol. Sci. 10:1989;218.
6. Akinaga S., Gomi K., Morimoto M., Tamaoki T., Okabe M. Cancer Res. 51:1991;4888.
7. Jackson J.R., Gilmartin A., Imburgia C., Winkler J.D., Marshall L.A., Roshak A. Cancer Res. 60:2000;566.
8. Rodrigues Pereira E., Belin L., Sancelme M., Prudhomme M., Ollier M., Rapp M., Sevère D., Riou J.F., Fabbro D., Meyer T. J. Med. Chem. 39:1996;4471.
9. Bailly C., Riou J.F., Colson P., Houssier C., Rodrigues-Pereira E., Prudhomme M. Biochemistry. 36:1997;3917.
10. Moreau P., Anizon F., Sancelme M., Prudhomme M., Sevère D., Riou J.-F., Goossens J.-F., Hénichart J.-P., Bailly C., Labourier E., Tazi J., Fabbro D., Meyer T., Aubertin A.-M. J. Med. Chem. 42:1999;1816.
11. Prudhomme M. Curr. Med. Chem. 7:2000;1189.
12. Moreau P., Anizon F., Sancelme M., Prudhomme M., Bailly C., Carrasco C., Ollier M., Sevère D., Riou J.-F., Fabbro D., Meyer T., Aubertin A.-M. J. Med. Chem. 41:1998;1631.
13. Ohe Y., Tanigawara Y., Fujii H., Ohtsu T., Wakita H., Igarashi T., Minami H., Eguchi K., Shinkai T., Tamura T., Kunotoh H., Saijo N., Okada K., Ogino H., Sasaki Y. Proc. ACSO. 16:1997;199. a.
14. Yoshinari T., Ohkubo M., Fukasawa K., Egashira S., Hara Y., Matsumoto M., Nakai K., Arakawa H., Morishima H., Nishimura S. Cancer Res. 59:1999;4271.
15. Goossens J.F., Kluza J., Vezin H., Kouach M., Briand G., Baldeyrou B., Wattez N., Bailly C. Biochem. Pharmacol. 65:2003;25.
16. Weitman S., Moore R., Barrera H., Cheung N.K., Izbicka E., Von Hoff D.D. J. Pediatr. Hematol. Oncol. 20:1998;136.
17. Dowlati A., Remick S.C., Majka S., Ingalls S., Hoppel C., Spiro T., Gerson S., Willson J.K.V. Proc. Am. Soc. Clin. Oncol. 18:1999;181. a.
18. Ohkubo M., Kojiri K., Kondo H., Tanaka S., Kawamoto H., Nishimura T., Nishimura I., Yoshinari T., Arakawa H., Suda H., Morishima H., Nishimura S. Bioorg. Med. Chem. Lett. 9:1999;1219.
19. Qu X., Chaires J.B., Fukasawa K., Nishimura S., Yoshinari T., Bailly C. Anti-Cancer Drug Des. 14:1999;433.
20. Carrasco C., Facompré M., Chisholm J.D., Van Vranken D.L., Wilson W.D., Bailly C. Nucleic Acids Res. 30:2002;1774.
21. Facompré M., Carrasco C., Colson P., Houssier C., Chisholm J.D., Van Vranken D.L., Bailly C. Mol. Pharmacol. 62:2002;1215.
22. Bailly C., Qu X., Anizon F., Prudhomme M., Riou J.F., Chaires J.B. Mol. Pharmacol. 55:1999;377.
23. Moreau P., Anizon F., Sancelme M., Prudhomme M., Bailly C., Sevère D., Riou J.F., Fabbro D., Meyer T., Aubertin A.M. J. Med. Chem. 42:1999;584.
24. Gartiser T., Selve C., Delpuech J.J. Tetrahedron Lett. 24:1983;1609.
25. Chen Y., Vogel P. J. Org. Chem. 59:1994;2487.
26. Anizon F., Moreau P., Sancelme M., Voldoire A., Prudhomme M., Ollier M., Sevère D., Riou J.F., Bailly C., Fabbro D., Meyer T., Aubertin A.M. Bioorg. Med. Chem. 6:1998;1597.
27. Gilbert E.J., Chisholm J.D., Van Vranken D.L. J. Org. Chem. 64:1999;5670.
28. Labourier E., Riou J.F., Prudhomme M., Carrasco C., Bailly C., Tazi J. Cancer Res. 59:1999;52.
29. Bailly C., Colson P., Houssier C., Rodrigues-Pereira E., Prudhomme M., Waring M. J. Mol. Pharmacol. 53:1998;77.
30. Bailly C., Carrasco C., Hamy F., Vezin H., Prudhomme M., Saleem A., Rubin E. Biochemistry. 38:1999;8605.
31. Tua A., Wang J., Kulpa V., Wernette C.M. Biochimie. 79:1997;341.
32. Malonne H., Atassi G. Anti-Cancer Drugs. 8:1997;811.
33. Bailly C., Dassonneville L., Colson P., Houssier C., Fukasawa K., Nishimura S., Yoshinari T. Cancer Res. 59:1999;2853.