Gram Scale Synthesis of Membrane-Active Antibacterial 4-Quinolone Lead Compound.

Autor: Jachak GR; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States., Orimoloye MO; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States., Aldrich CC; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 May 05; Vol. 88 (9), pp. 6209-6217. Date of Electronic Publication: 2023 Apr 18.
DOI: 10.1021/acs.joc.3c00239
Abstrakt: An improved method for the synthesis of a new quinolone class of antibiotics, which are exceptionally potent against gram-positive bacteria, has been developed and the structure confirmed by single-crystal X-ray analysis. In the course of synthesis, using either Chan-Lam coupling or Buchwald-Hartwig amination, we have shown that the careful choice of protecting group at the C4 position of the quinoline is required for selective amination at the C5 position and subsequent deprotection to avoid the formation of a novel pyrido[4,3,2- de ]quinazoline tetracycle.
Databáze: MEDLINE