Related Experiment Video
Updated: May 28, 2026

Visualization of Bacterial Resistance using Fluorescent Antibiotic Probes
Published on: March 2, 2020
Synthesis of macrolones with central piperazine ring in the linker and its influence on antibacterial activity
Samra Kapić1, Hana Cipčić Paljetak, Ivana Palej Jakopović
1GlaxoSmithKline Research Centre Zagreb, Croatia. samra.kapic@glpg.com
Abstract:
Three macrolides, clarithromycin, azithromycin and 11-O-Me-azithromycin have been selected for the construction of a series of new macrolone derivatives. Quinolone-linker intermediates are prepared by Sonogashira-type C(6)-alkynylation of 6-iodoquinolone precursors. The final macrolones, differing by macrolide moiety and substituents at the position N-1 of the quinolone or by the presence of an ethyl ester or free acid on the quinolone unit attached via a linker. The linker comprises of a central piperazine ring bonded to the 4″-O position of cladinose by 3-carbon ester or ether functionality. Modifications of the linker did not improve antibacterial properties compared to the previously reported macrolone compounds. Linker flexibility seems to play an important role for potency against macrolide resistant respiratory pathogens.
Related Concept Videos
Inhibitors of Gram-positive Cell Wall Synthesis
Inhibitors of Bacterial Protein Synthesis
Production of Antibiotics
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Combined Effects of Drugs: Synergism
Such synergistic combinations...
Mechanism of Antibiotic Resistance in MRSA
