Iron transport-mediated drug delivery: Synthesis and biological evaluation of cyanuric acid-based siderophore analogs and β-lactam conjugates

Article abstract of DOI:10.1021/jo00084a018

Trihydroxamate-containing isocyanurates 4a-c were synthesized and determined to be capable of substituting for natural siderophores (microbial iron sequestering agents) in limited microbiological assays. The direct coupling of protected 4a to carbacephalosporins 16 and 17 and subsequent deprotection gave conjugates 20 and 21. The Lorabid conjugate 21 was especially active against E. ccoli X580 in preliminary biological tests, thus demonstrating the continued potential of siderophore-mediated drug delivery.