Synthesis, structural characterization and antimicrobial activities of cyclochlorotriphosphazene derivatives derived from N-(1-Naphthyl)ethylenediamine

Abstract

The nucleophilic substitution reactions of cylochlorotriphosphazene (N₃P₃Cl₆) with N-(1-Naphthyl)ethylenediamine resulted in the following formation of partially and fully substituted cyclotriphosphazene derivatives: 2,4,4,6,6-pentachloro-2-open-chain-N-(1-Naphthyl) ethylendiamino-cyclotriphosphazatriene (3); 4,4,6,6-tetrachloro-2,2-spiro-N-(1-Naphthyl) ethylendiamino-cyclotriphosphazatriene (4); 2,6,6-trichloro-2-open-chain-4,4-spiro-N-(1-Naphthyl)ethylendiamino-cyclotriphosphazatriene (5); 2,4-dichloro-2,4-ansa-6,6-spiro-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (6); and 2,4,6-trichloro-2,4,6-non-gem-open-chain-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (7); 2,2,4,4,6,6-tri-spiro-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (8); 2,4-dichloro-2,4-cis-open-chain-6,6-spiro-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (9); and 2,4,6,6-tetrachloro -2,4-ansa-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (10). The reactions produced the 4,4,6,6-tetrachloro-2,2-spiro-N-(1-Naphthyl) ethylendiamino-cyclotriphosphazatriene (4) and 2,4,6,6-tetrachloro-2,4-ansa-N-(1-Naphthyl)ethylendiamino)-cyclotriphosphazatriene (10) derivatives as the major products in this system. The structures of the compounds were characterized by FT-IR, elemental analysis, TLC-MS, FT-IR, ¹H, and ³¹P NMR spectral data. All the derived compounds (3–10) were screened for antimicrobial activity by using the broth-agar microdilution technique for the determination of MIC and MCC values. In this context, the compounds were examined against three different human pathogens; Escherichia coli W3110, Staphylococcus aureus ATCC 25923 and Candida albicans ATCC 10231. Except compounds 6 and 9, the rest of the compounds exhibited significant antimicrobial activity on E. coli (W3110), S. aureus (ATCC 25923) and C. albicans (ATCC 1023). Among the synthesized derivatives, compound 4 is the most active agent against the referenced bacteria.

Graphical Abstract

Keywords:

• Cyclotriphosphazene
• N-(1-naphtyl)ethylenediamine
• antimicrobial activity
• Escherichia coli W3110
• Candida albicans ATCC 10231

Acknowledgment

We are indebted to the School of Chemistry/Southampton University for providing a fully facilitated academic visitor’s research placement and for obtaining spectroscopic data. The authors would also like to extend their thanks to Bilecik Şeyh Edebali University for their financial support to this study.