New class of diethyl substituted phosphoramidimidates and phosphonimidates: synthesis, spectral characterization and antimicrobial activity

Abstract

A series of new class of diethyl N-2-hydroxyethyl-N'-substituted phosphoramidimidates 6(a–e) and diethyl P-morpholino-N-substituted phosphonimidates 6(f–j) was synthesized. The precursor intermediates, diethyl substituted phosphoramidites 3(a–b) were prepared initially by a reaction of various amines 1(a–b) and diethyl phosphorochloridite (2) and then they were treated by in situ with aromatic/alkyl azides through Staudinger reaction to accomplish title products. Structures of all the synthesized compounds were characterized by spectroscopic data such as IR, NMR (¹H, 13C, ³¹P), mass, and elemental analyses. The synthesized compounds were screened for their in vitro antimicrobial activity to understand their biological potency. The biological screening results disclosed that compounds 6b, 6c, 6e, 6g, 6h and 6j having potent antimicrobial activity against all the tested pathogens.

Graphical Abstract

Keywords:

• Iminophosphoranes
• diethyl phosphorochloridite
• Staudinger reaction
• antimicrobial activity

Acknowledgements

The author (M. Varalakshmi) is grateful to acknowledge University Grants Commission [RGNF, F1-17.1/2011-12] for financial support under which this research was carried out. The author would like to thank the Department of Biochemistry, S. V. University for evaluating the antimicrobial activity.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The author (M. Varalakshmi) is grateful to acknowledge University Grants Commission [RGNF, F1-17.1/2011-12] for financial support under which this research was carried out. The author would like to thank the Department of Biochemistry, S. V. University for evaluating the antimicrobial activity.