Pyridinium salts of dithiophosphoric acids on the basis of nicotinic acids and their isomers, 3-hydroxypyridine, and 3-pyridinemethanol

Abstract

A new series of chiral carboxypyridinium dithiophosphates were synthesized by the reactions of nicotinic, isonicotinic, and picolinic acids with dithiophosphoric acid on the basis (1S)-endo-(–)-borneol in benzene or ethanol. 5,5-Dimethyl-2-mercapto-2-thiono-1,3,2-dioxaphosphorinane reacted with 3-hydroxypyridine or 3-pyridinemethanol in EtOH to afford the 3-hydroxypyridinium and 3-hydroxymethylpyridinium 5,5-dimethyl-2-mercapto-2-thiono-1,3,2-dioxaphosphorinanes which possessed antifungal activity against Candida albicans.

Graphical Abstract

Keywords:

• Pyridine alkaloids
• dithiophosphoric acids
• ionic liquids
• antimicrobial activity

Acknowledgements

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.

Additional information

Funding

This work was funded by the Russian Foundation for Basic Research (grant no. 18-415-160012-р_Volga Region_а).