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Synthesis and antibacterial activity of C6-carbazate ketolides

A novel series of ketolides containing various heteroaryl groups linked to the macrolide core via a C6-carbazate functionality has been successfully synthesized. Select compounds of this series display in vitro and in vivo (sc dosing) activity comparable to telithromycin. A novel series of ketolides...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2006-12, Vol.16 (24), p.6231-6235
Main Authors: Tennakoon, Manomi A., Henninger, Todd C., Abbanat, Darren, Foleno, Barbara D., Hilliard, Jamese J., Bush, Karen, Macielag, Mark J.
Format: Article
Language:English
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Summary:A novel series of ketolides containing various heteroaryl groups linked to the macrolide core via a C6-carbazate functionality has been successfully synthesized. Select compounds of this series display in vitro and in vivo (sc dosing) activity comparable to telithromycin. A novel series of ketolides containing heteroaryl groups that are linked to the erythronolide ring via a C6-carbazate functionality has been successfully synthesized. Careful modulation of the heteroaryl groups, the length and degree of saturation of the C6-carbazate linker, and the substituents present on each of the carbazate nitrogens led to compounds with potent activity against key bacterial respiratory pathogens. The best analogs of this series had in vitro and in vivo (sc dosing) profiles that were comparable to telithromycin.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2006.09.036