Design, organocatalytic synthesis, and bioactivity evaluation of enantiopure fluorinated LpxC inhibitors

Melanie Rodríguez-Alvarado, Riccardo Russo, Nancy D. Connell, Stacey E. Brenner-Moyer

Research output: Contribution to journalArticlepeer-review

Abstract

Enantiopure compounds with a strategically incorporated fluorine atom intended to enhance LpxC inhibition have been synthesized using an organocascade fluorination reaction as the key step. These are the first low molecular weight LpxC inhibitors to contain a fluorine atom on a critically important chiral center that is substituted with two pharmacophoric moieties, and were thusly designed to provide new SAR data for this class of compounds. Fluorinated compounds were evaluated against ESKAPE pathogens and exhibited MICs of ≤12.5 μg mL-1 against Pseudomonas aeruginosa.

Original languageEnglish (US)
Pages (from-to)5867-5878
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number30
DOIs
StatePublished - Aug 14 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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