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

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

Keywords:

• Pyridoxine
• phosphorus dithioacids
• antimicrobial activity

Acknowledgment

The authors are grateful to the staff of Distributed Spectral-Analytical Center of Shared Facilities for Study of Structure, Composition, and Properties of Substances and Materials of Federal Research Center of Kazan Scientific Center of Russian Academy of Sciences for their research and assistance in discussing the results.