This talk will feature our recent advances in the study of bacterial 2-alkyl-4(1H)-quinolones and their N-oxide derivatives. These compounds, produced by various bacterial species, serve a broad range of functions, from signaling to antimicrobial activities. Beyond enhancing the mechanistic understanding of their biosynthesis and phylogeny, I will focus on their potential as novel scaffolds for highly specific, ultra-narrow-spectrum antibiotics. Our research demonstrates that NQNO, along with its synthetic derivatives, can disrupt the electron transport chain and subsequently destabilize a toxin-antitoxin system of the human-specific pathogen Neisseria gonorrhoeae. This system is present in pathogenic Neisseria gonorrhoeae but absent in commensal strains, making our compounds highly selective in targeting the pathogen.