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Synthesis, ribosomal selectivity, and antibacterial activity of netilmicin 4′-derivatives

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Abstract

Halogenation of a suitably protected netilmicin derivative enables preparation of 4′-chloro-, bromo-, and iodo derivatives of netilmicin after deprotection. Suzuki coupling of a protected 4′-bromo derivative with phenylboronic acid or butyltrifluoroborate affords the corresponding 4′-phenyl and 4′-butyl derivatives of netilmicin. Sulfenylation of suitably protected netilmicin derivative with ethanesulfenyl chloride followed by deprotection affords 4′-ethylsulfanylnetilmicin. All netilmicin 4′-derivatives displayed reduced levels of inhibition for prokaryotic ribosomes and reduced antibacterial activity against typical Gram-positive and Gram-negative strains. None of the derivatives displayed enhanced target selectivity.

Graphical abstract: Synthesis, ribosomal selectivity, and antibacterial activity of netilmicin 4′-derivatives

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Publication details

The article was received on 11 Mar 2019, accepted on 19 Apr 2019 and first published on 25 Apr 2019


Article type: Research Article
DOI: 10.1039/C9MD00153K
Med. Chem. Commun., 2019, Advance Article

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    Synthesis, ribosomal selectivity, and antibacterial activity of netilmicin 4′-derivatives

    A. Sonousi, D. Shcherbakov, A. Vasella, E. C. Böttger and D. Crich, Med. Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9MD00153K

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