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Medchemcomm. 2019 Apr 25;10(6):946-950. doi: 10.1039/c9md00153k. eCollection 2019 Jun 1.

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

Author information

1
Department of Chemistry , Wayne State University , 5101 Cass Avenue , Detroit , MI 48202 , USA . Email: dcrich@chem.wayne.edu.
2
Institut für Medizinische Mikrobiologie , Universität Zürich , 28 Gloriastrasse , 8006 Zürich , Switzerland.
3
Laboratorium für Organische Chemie , ETH Zürich , Vladimir-Prelog-Weg 1-5/10 , 8093 Zürich , Switzerland.

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.

PMID:
31303992
PMCID:
PMC6595968
[Available on 2020-04-25]
DOI:
10.1039/c9md00153k

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