Istuk Zorica Marusić, Mutak Stjepan, Kujundzić Nedjeljko, Kragol Goran
GlaxoSmithKline Research Centre Zagreb, Prilaz B. Filipovića 29, Zagreb, Croatia.
Bioorg Med Chem. 2007 Jul 1;15(13):4498-510. doi: 10.1016/j.bmc.2007.04.021. Epub 2007 Apr 19.
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.
已开发出一种高效合成15元氮杂内酯的多种9a-氨基甲酰基和9a-硫代氨基甲酰基-3-去克拉定糖基-6-羟基以及3-去克拉定糖基-6-甲氧基衍生物的方法。这些衍生物在9a位通过脲或硫脲部分连接到大环内酯支架上带有各种烷基和芳基基团。C-3位羟基的化学转化得到了一系列酮内酯、酸酐、半缩酮、环醚和酰化物。结果表明，在其他相同反应条件下，6-羟基和6-甲氧基衍生物会发生不同的化学转化。对所制备化合物的抗菌性能进行了评估。
