SYNTHESIS OF NOVEL CITRATE-BASED SIDEROPHORES AND SIDEROPHORE-BETA-LACTAM CONJUGATES - IRON TRANSPORT-MEDIATED DRUG-DELIVERY SYSTEMS

被引:24
作者
GHOSH, A [1 ]
MILLER, MJ [1 ]
机构
[1] UNIV NOTRE DAME,DEPT CHEM & BIOCHEM,NOTRE DAME,IN 46556
关键词
D O I
10.1021/jo00079a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of analogs of arthrobactin (5), a microbial iron chelator, and its imide 8 are described. The differentially protected citric acid residue 31 served as the key intermediate in making conjugates having a generalized structure 14 with two representative carbacephalosporin units, 15 and 16. Both conjugates, 49 and 51, showed antibiotic activity, while conjugate 51 obtained from beta-lactam 16 bearing a phenylglycyl side chain was shown to be more effective.
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收藏
页码:7652 / 7659
页数:8
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