Pyridoxonium salts of chiral and cyclic dithiophosphoric and bisdithiophosphonic acids and their antimicrobial activities

Abstract

Abstract Pyridoxonium salts of chiral linear and cyclic dithiophosphoric acids were obtained by the reactions of pyridoxine with bis{2-О-[2-methyl-(2S)-3-O-propionyl]}, bis{2-О-[1,4-О,О-dimethyl-(2S)-succinyl]}, and O,O-di-2-butyl dithiophosphoric acids, and cyclic dithiophosphoric acids of 1,3,2-dioxaphosphorinane, 1,3,2-dioxaphospholane, and 1,3,2-dioxaphosphepin structure. Syntheses of acetonide pyridoxonium О,О-dimenthyl dithiophosphates were carried out by the reaction of seven-membered pyridoxine acetonide with О,О-dimenthyl dithiophosphoric acids obtained from (–)-(1 R,2S,5R)-menthol and (+)-(1S,2R,5S)-menthol. Diacetonide pyridoxonium bisdithiophosphonate was also prepared. The antibacterial and antifungal activities of pyridoxonium chiral linear and cyclic dithiophosphates were evaluated. Graphical Abstract