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2004
Antibiotics
U 1200
47- 204
Synthesis and Antibacterial Activity of Novel Bifunctional Macrolides. —
To probe the space around the macrolide molecule and to create additional interactions
with a secondary site on the ribosome, two large lead generation libraries of macrolides
attached to a variety of tethers and potential secondary binders are prepared. Diamines
are selected as bifunctional units, linking the macrolide and the secondary binder. The
secondary binders are selected to mimic parts of known antibiotics that bind to domains
II and/or V. The 3-O-carbamate analogues show a weak antibacterial profile while the
9-oxime series, e.g. (I), displays a distinct profile. Macrolides (I) are not active in erythromycin-susceptible S. aureus, but they exhibit improved activity against the S. aureus
strain possessing the erm mechanism of resistance, and they are very active against susceptible and resistant S. pneumoniae strains. — (AKRITOPOULOU-ZANZE*, I.;
PHELAN, K. M.; MARRON, T. G.; YONG, H.; MA, Z.; STONE, G. G.; DALY, M. M.;
HENSEY, D. M.; NILIUS, A. M.; DJURIC, S. W.; Bioorg. Med. Chem. Lett. 14
(2004) 14, 3809-3813; Abbott Lab., Global Pharm. R&D, Abbott Park, IL 60064,
USA; Eng.) — H. Hoennerscheid
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