New rifabutin analogs: Synthesis and biological activity against Mycobacterium tuberculosis

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 22, 2006, Pages 5717-5722

  Barluenga, José ^a   Aznar, Fernando ^a   García, Ana Belén ^a   Cabal, María Paz ^a   Palacios, Juan J ^b   Menéndez, María Angela ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b HOSPITAL UNIVERSITARIO CENTRAL DE ASTURIAS   (Spain)

Author keywords

Mycobacterium tuberculosis; Rifabutin; Rifamycins; Rifastures

Indexed keywords

RIFABUTIN; RIFAMPICIN; RIFAMYCIN DERIVATIVE; RIFASTURES; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BIOLOGICAL ACTIVITY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; MYCOBACTERIUM KANSASII; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

ANTIBIOTICS, ANTITUBERCULAR; DRUG RESISTANCE, MICROBIAL; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM AVIUM COMPLEX; MYCOBACTERIUM KANSASII; MYCOBACTERIUM TUBERCULOSIS; RIFABUTIN; RIFAMPIN;

MYCOBACTERIUM KANSASII; MYCOBACTERIUM TUBERCULOSIS;

EID: 33749260712     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.08.090     Document Type: Article

References (45)

1. Sensi P., Margalith P., and Timbal M. Fármaco, Ed. Sc. 14 (1959) 146
2. Riva S., and Silvestri L.G. Annu. Rev. Microbiol. 26 (1972) 199
3. Lounis N., and Rosceigno G. Curr. Pharm. Des. 10 (2004) 3229
4. Floss H.G., and Yu T.-W. Chem. Rev. 105 (2005) 621
5. Prelog V., and Oppolzer W. Helv. Chim. Acta 56 (1973) 2279
6. Gallo G.G., Martinelli E., Pagani V., and Sensi P. Tetrahedron 30 (1974) 3093
7. Bartolucci C., Cellai L., Di Filippo P., Segre A., Brufani M., Filocamo L., Brizzi V., Benedetto A., Di Caro A., and Elia G. Il Fármaco 47 (1992) 1367
8. Bartolucci C., Cellai L., Di Filippo P., Ianelli M., Segre A., Brufani M., Filocamo L., Bianco A., Guiso M., Brizzi V., and Benedetto A. Pharm. Pharmacol. Lett. 3 (1993) 1
9. Umezawa H., Mizuno S., Yamazaki H., and Nitta K. J. Antibiot. 21 (1968) 234
10. Sippel A., and Hartmann G. Biochim. Biophys. Acta 157 (1968) 218
11. Wehrli W., and Staehelin M. Bacteriol. Rev. 35 (1971) 290
12. Cellai L., Heumann H., Baer G., and Werel W. Eur. J. Med. Chem. 24 (1989) 105
13. Wehrli W., Knüsel F., Schmid K., and Staehelin M. Proc. Natl. Acad. Sci. U.S.A. 61 (1968) 667
14. Wehrli V., and Staehelin M. Biochim. Biophys. Acta 182 (1969) 24
15. Sensi P. Pure Appl. Chem. 41 (1975) 15
16. Sensi P., Maggi N., Füresz S., and Maffii G. Antimicrob. Agents Chemother. (1966) 699-714
17. Lancini G., and Zanichelli W. Structure-Activity Relationship among the Semisynthetic Antibiotics. In: Perlmann D. (Ed) (1977), Academic Press, New York 531-600
18. Other trivial names used are: rifamycin AMP and rifaldazine.
19. Maggi N., Pasqualucci C.R., Ballota R., and Sensi P. Chemotherapy 11 (1966) 285
20. Gallo G.G., and Radaelli P. Analytical Profiles of Drug Substances. In: Florey E.K. (Ed) (1976), Academia Press, New York 467-513
21. Abbreviated name for 3-amino-4-deoxo-4-imino-3,4-imidazolinyl-1H-[2-spiro(4- piperidyl)]rifamycin S.
22. Sanfilippo A., Della Bruna C., Marsili L., Morvillo E., Pasqualucci C.R., Schioppacasi G., and Ungheri D. J. Antibiot. 33 (1980) 1193
23. Marsili L., Pasqualucci C.R., Vigevani A., Gioia B., Schioppacassi G., and Oronzo G. J. Antibiot. 34 (1981) 1033
24. Medeiros, M.; Costa, M.; Figueiredo, M.; Rosa, M.; Curto, M.; Santos, L.; Crus, M.; Gaspar, M.; Feio, S. WO 2004/005298 A1.
25. Marsili, L.; Rosetti, V.; Pasqualucci, C.R. US Patent 4,086,225, 1978.
26. Marsili, L.; Rossetti, V.; Pasqualucci, C.R. German Patent Appl. 2,825,445, 1979.
27. Marsili, L.; Rosetti, V.; Pasqualucci, C.R. US Patent 4,219,478, 1980.
28. Della Bruna C., Schioppacassi G., Ungheri D., Jabes D., Morvillo E., and Sanfilippo A. J. Antibiot. 36 (1983) 1502
29. Kunin C.M. Clin. Infect. Dis. 22 (1996) S3
30. Chaisson R.E. Clin. Infect. Dis. 22 (1996) S61
31. Ungheri C.D., Della Bruna C., and Sanfilippo A. M. Tuberculosis Drugs Exp. Clin. Res. 10 (1984) 681
32. Ungheri D., Della Bruna C., and Sanfilippo A. G. Ital. Chemioterapic 31 (1984) 211
33. Espinal M.A., Kim S.J., Suárez P.F., Kam K.M., Khomenko A.G., Migliori G.B., et al. JAMA 283 (2000) 2537
34. Gardner C.A., Acharya T., and Pablos-Méndez A. Clin. Chest. Med. 26 (2005) 341
35. Rieder, H.L. Intervetions for Tuberculosis Control. International Union against Tuberculosis and Lung Disease, Paris, France, 2002.
36. Spanish Patent ES 2 246 155 A1, 2005. International Patent PCT WO 2006/027397 A1.
37. Obtained from Rifamycin S according to different procedures: Marsili, L.; Rosseti, V.; Pasqualucci, C. US Patent 4,017,481, 1977.
38. Rossetti, V.; Marsili, L. D.E. Patent 2847427, 1979.
39. Marchi, E.; Montecchi, L. G.B. Patent 2009744, 1979.
40. Barluenga J., Aznar F., Valdés C., and Cabal M.-P. J. Org. Chem. 58 (1993) 3391
41. Garci{dotless}́a A.-B., Valdés C., and Cabal M.-P. Tetrahedron Lett. 45 (2004) 4357
42. Rubio E., Merino I., Garci{dotless}́a A.-B., Cabal M.-P., Ribas C., and Bayod-Jasanada M. Magn. Reson. Chem. 43 (2005) 269
43. The results of this experiment showed that the configuration at the spiranic carbon does not improve biological activity against the susceptible strains (entries 2-6, Table 2), and that bioactivity is diminished considerably against the resistant TB strain (entries 1 and 7, Table 2). Based on these findings, we do not feel that it would be warranted to check the activity of the other five minor isomers.
44. Canetti G., Rist N., and Grosset J. Rev. Tuberc. Pneumol. 27 (1963) 217
45. Rothstein D.M., Hartman A.D., Cynamon M.H., and Eisenstein B.H. Expert Opin. Investig. Drugs 12 (2003) 255