Synthesis, spectral properties, and antibacterial activity of synthetic precursors of macrocyclic oxa- and thia-substituted benzolactones and benzoketones.
Terminally difunctional compounds were synthesized by alkylation of salicylic acid, thiosalicylic acid (o-mercaptobenzoic acid), or their derivatives. Whereas methyl salicylate and thiosalicylic acid were smoothly etherified, salicylic acid was alkylated at the carboxyl. Characteristic IR and NMR spectral patterns in the synthesized compounds can be attributed to intramolecular hydrogen bonding or substituent effects and are consistent with observations already reported for similar compounds. Three synthesized compounds exhibited low but reproducible inhibitory effects on Bacillus subtilis growth.
D001412:Bacillus subtilis / Q000187:drug effects*; D007659:Ketones / Q000032:analysis / Q000138:chemical synthesis / Q000494:pharmacology; D007783:Lactones / Q000032:analysis / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D012459:Salicylates / Q000032:analysis; D013055:Spectrophotometry, Infrared
D007659:Ketones; D007783:Lactones; D012459:Salicylates