Synthesis of two and antibacterial activity of one novel oxime ether derivatives of erythromycin A

Farmaco

Volumn 58, Issue 10, 2003, Pages 1011-1015

  Dondas, H A ^a   Yaktubay, N ^b  

^a MERSIN UNIVERSITY   (Turkey)

^b CUKUROVA UNIVERSITY   (Turkey)

Author keywords

Erythromycinerythromycin oxime ether; Michael addition

Indexed keywords

9 O (2 ETHENESULFONYLETHYL)OXIME; 9 O (3 OXOBUTYL)OXIME; ERYTHROMYCIN DERIVATIVE; KETONE; OXIME; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; MICHAEL ADDITION; NONHUMAN;

EID: 0141514670     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00194-0     Document Type: Article

References (25)

1. Washington J.A., Wilson W.R. Erythromycin A microbial and clinical perspective after 30 year of clinical use. Mayo Clin. Proc. 60:1985;189.
2. Fernandes P.B., Neu H.C. The macrolide revival: thirty-five years after erythromycin. The Antimicrobic Newsletter. 4:1987;27-35.
3. Mao J.C.H., Putterman M. The intermolecular complex of erythromycin and ribozome. J. Mol. Biol. 44:1969;347-352.
4. Burger S. Wolf M.E. Medicinal Chemistry and Drug Discovery. 2:1995;481 Wiley, USA.
5. J.F. Chantot, J.C. Gasc, S.G. D'Ambrieres and A. Lutz, New ether oxime derivatives of erythromycin A: preparation and antibacterial activities, Program and Abstracts of the 23rd Interscience Conference on Antimicrobial Agents Chemotherapy, No. 447, P 165, Las Vegas, October 24-26, 1983.
6. Chantot J.F., Bryskier A., Gasc J.C. Antibacterial activities of roxithromycin: a laboratory evaluation. J. Antibiotics. 39:1986;660-668.
7. Wildsmith E. The reaction of erythromycin hydrazone with nitrous acid a new route to erythromycylamine. Tetrahedron Lett. 1:1972;29-30.
8. Massey E.H., Kitchel B.S., Martin L.D., Gerzon K. Antibacterial activity of 9(S)-erythromycylamine-aldehyde condensation product. J. Med. Chem. 17:1974;105-107.
9. Massey E.H., Kitchel B.S., Martin L.D., Gerzon K., Murphy H.W. Erythromycylamine. Tetrahedron Lett. 2:1970;157-160.
10. Lartey P.A., Deninno S.L., Faghih R., Hardy D.J., Clement J.J., Plattner J.J. Synthesis and activity of C-21 alkylamino derivatives of (9R)-erythromycylamine. J. Antibiot. 45:1992;380-385.
11. Hunt E., Knowles D.J.C., Shillingford C., Zomaya I.I. Erythromycin A 11, 12-methylene acetal. J. Antibiot. 40:1988;1644-1648.
12. Egan R.S., Freigberg L.A., Washburn W.H. Configuration of 9-imino derivatives of erythromycin. J. Org. Chem. 39:1974;2492-2494.
13. Brain E.G., Forrest A.K., Hunt E., Shillingford C., Wilson J.M. Erythromycin A oxime 11, 12-carbonate and its oxime ethers. J. Antibiot. 41:1989;1817-1822.
14. Nishimoto A., Narita K., Ohimoto S., Takahashi Y., Yoshizumi S., Yoshida T., Kado N., Okezaki E., Kato H. Studies on macrolide antibiotics I. Synthesis and antibacterial activity of erythromycin A 9-O-substituted oxime ether vderivatives against Mycobacterium avium complex. Chem. Pharm. Bull. 49:2001;1120-1127.
15. Gasc J.C., D'Ambrieres S.G., Lutz A., Chantot J.F. New ether oxime derivatives of erythromycin A a structure-activity relationship study. J. Antibiot. 44:1991;313-325.
16. Armstrong P., Grigg R., Taylor W.J. Cycloaddition reactions of oximes; powerful new carbon-carbon bond forming methodology. J. Chem. Soc. Chem. Commun. 1987;1325-1327.
17. Armstrong P., Grigg R., Surendrakumar S., Warnock W.J. Tandem intramolecular Michael addition and 1,3-dipolar cycloaddition reactions of oximes; versatile new carbon-carbon bond forming methodology. J. Chem. Soc. Chem. Commun. 1987;1327-1328.
18. Schumann E.L., Paquette L.A., Heinzelmann R.V., Wallach D.P., DaVanzo J.P., Greig M.E. The synthesis g-aminobutyric acid transaminase inhibition of aminooxy acids and related compound. J. Med. Pharm. Chem. 1962;464-477.
19. Morimoto S., Misawa Y., Adachi T., Nagate T., Watanabe Y., Omura S. Chemical modification of erythromycins. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A. J. Antibiot. XLIII:1990;286-294.
20. McGill J.M., Johnson R. Structrural and conformational analysis of (E)-erythromycin A oxime. Magnet. Reson. Chem. 31:1993;273-277.
21. Everett J.R., Tyler J.W. The conformational analysis of erythromycin A. J. Chem. Soc. Perkin Trans. 2:1987;1659-1667.
22. 13C NMR spectra. J. Chem. Soc. Perkin Trans. 2:1991;1489-1494.
23. Everett J.R., Hunt E., Tyler J.W. Ketone-hemiacetal tautomerism in erythromycin A in non-aqueous solutions. An NMR spectroscopic study. J. Chem. Soc. Perkin Trans. 2:1991;1481-1487.
24. Some parts of this work were presented at the Second International Meeting on Pharmacy and Pharmaceutical Sciences, Istanbul, Turkey, 6-9 September, 1998.
25. H.A. Dondas, Biochemical Application of Oxime Nitrone Cycloaddition Cascades, Ph.D. thesis Leeds University, Leeds, UK, 1997.