Novel 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 6-methoxy derivatives of 15-membered macrolides.

Autor: Istuk ZM; GlaxoSmithKline Research Centre Zagreb, Prilaz B. Filipovića 29, Zagreb, Croatia., Mutak S, Kujundzić N, Kragol G
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2007 Jul 01; Vol. 15 (13), pp. 4498-510. Date of Electronic Publication: 2007 Apr 19.
DOI: 10.1016/j.bmc.2007.04.021
Abstrakt: An efficient method for the synthesis of diverse 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 3-decladinosyl-6-methoxy derivatives of 15-membered azalides has been developed. These derivatives bear various alkyl and aryl groups attached to macrolide scaffold through urea or thiourea moieties at 9a position. Chemical transformations of hydroxy group at position C-3 afforded range of ketolides, anhydrolides, hemiketals, cyclic ethers, and acylides. It has been shown that 6-hydroxy and 6-methoxy derivatives undergo different chemical transformations under otherwise identical reaction conditions. Antimicrobial properties of prepared compounds were evaluated.
Databáze: MEDLINE