Journal article

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

  • Sonousi A Department of Chemistry , Wayne State University , 5101 Cass Avenue , Detroit , MI 48202 , USA . Email: dcrich@chem.wayne.edu.
  • Shcherbakov D Institut für Medizinische Mikrobiologie , Universität Zürich , 28 Gloriastrasse , 8006 Zürich , Switzerland.
  • Vasella A Laboratorium für Organische Chemie , ETH Zürich , Vladimir-Prelog-Weg 1-5/10 , 8093 Zürich , Switzerland.
  • Böttger EC Institut für Medizinische Mikrobiologie , Universität Zürich , 28 Gloriastrasse , 8006 Zürich , Switzerland.
  • Crich D Department of Chemistry , Wayne State University , 5101 Cass Avenue , Detroit , MI 48202 , USA . Email: dcrich@chem.wayne.edu.
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  • 2019-07-16
Published in:
  • MedChemComm. - 2019
English 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.
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  • English
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https://sonar.ch/global/documents/238596
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