Preparation and in vitro antibacterial activity of 9-O-glycosyloxime derivatives of erythromycin A, a new class of macrolide antibiotics

Journal of Antibiotics

Volumn 49, Issue 10, 1996, Pages 1036-1043

  Grandjean, Cyrille ^a   Lukacs, Gabor ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ERYTHROMYCIN; ERYTHROMYCIN DERIVATIVE; OXIME DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HAEMOPHILUS INFLUENZAE; MORAXELLA CATARRHALIS; NONHUMAN; PRIORITY JOURNAL; STREPTOCOCCUS PNEUMONIAE;

EID: 0029801622     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.49.1036     Document Type: Article

References (15)

1. WASHINGTON, J. A., II & W. R. WILSON: Erythromycin A: A microbial and clinical perspective after 30 years of clinical use (first of two parts). Mayo Clin. Proc. 60: 189-203, 1985
2. WASHINGTON, J. A., II & W. R. WILSON: Erythromycin A: A microbial and clinical perspective after 30 years of clinical use (second of two parts). Mayo Clin. Proc. 60: 271-278, 1985
3. LARTEY, P. A. & R. FAGHIH: Recent progress in the chemical modification of erythromycin. In Recent progress in the chemical synthesis of antibiotics and related microbial products. Ed., G. LUKACS, Vol. 2, pp. 121-140, Springer-Verlag, Berlin, Heidelberg, New York, London, Paris, Tokyo, Hong Kong, Barcelona, Budapest, 1993
4. DANAN, G.; V. DESCATOIRE & D. PESSAYRE: Self induction by erythromycin and its own transformation into metabolite forming an inactive complex with reduced cytochrome P450. J. Pharmacol. Exp. Ther. 218: 509-514, 1981
5. BABANY, G.; D. LARREY & D. PESSAYRE: Macrolide antibiotics as inducers and inhibitors of cytochrome P450 in experimental animals and man. In Progress in drug metabolism. Ed., G. G. GIBSON, pp. 61-98, Taylor and Francis, London, 1988
6. SAKAKIBARA, H. & S. ŌMURA: Chapter 3. Chemical modification and structure-activity relationship of macrolides. In Macrolide antibiotics. Chemistry, biology and practice. Ed., S. ŌMURA, pp. 85-125, Academic Press, New-York, 1984
7. DELAFORGE, M.; P. LADAM, G. BOUILLÉ, J. GHARBI-BENAROUS, M. JAOUEN & J. P. GIRAULT: pH effects on the N-demethylation and formation of the cytochrome P450 iron II nitrosoalkane complex for erythroycin derivatives. Chem.-Biol. Interactions 85:215-227, 1992
8. DELAFORGE, M.; M. JAOUEN & D. MANSUY: Dual effects of macrolide antibiotics on rat liver cytochrome P-450. Induction and formation of metabolite-complexes: A structure-activity relationship. Biochem. Pharmacol. 32: 2309-2318, 1983
9. GHARBI-BENAROUS, J.; P. LADAM, M. DELAFORGE & J. P. GIRAULT: Conformational analysis of major metabolites of macrolide antibiotics roxithromycin and erythromycin A with different biological properties by NMR spectroscopy and molecular dynamics. J. Chem. Soc., Perkin Trans. 2: 2303-2315, 1993
10. GASC, J. C.; S. GOUIN D'AMBRIÈR̀ES, A. LUTZ & J. F. CHANTOT: New ether oxime derivatives of erythromycin A. A structure-activity relationship study. J. Antibiotics 44:313-330, 1991
11. N2 displacement of carbohydrate triflates by 9-oximes of erythromycin A and of a tylosin derivative. J. Carbohydr. Chem.: in the press.
12. WATANABE, Y; M. KASHIMURA, T. ASAKA, T. ADACHI & S. MORIMOTO: Chemical modifications of erythromycin. X. Removal of benzyloxycarbonyl and 2-chlorobenzyl groups of erythromycin derivatives by use of catalytic transfer hydrogenation. Heterocycles 36:761-768, 1993
13. WATANABE, Y.; S. MORIMOTO, T. ADACHI, M. KASHIMURA & T. ASAKA: Chemical modifications of erythromycin. XI. Selective methylation at the C-6 hydroxyl group of erythromycin A oxime derivatives and preparation of clarithromycin. J. Antibiotics 46: 647-660, 1993
14. NAGATE, T.; Y. WATANABE & S. ŌMURA: Chemical modification of erythromycins. II. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A. J. Antibiotics 43: 286-294, 1990
15. MASSEY, E. H.; B. KITCHELL, L. D. MARTIN, K. GERZON & H. W. MURPHY: Erythromycylamine. Tetrahedron Lett. 2: 157-160, 1970