Research Information System
New Journal of Chemistry, vol.49, no.36, pp.15866-15884, 2025 (SCI-Expanded)
Hexachlorocyclotriphosphazene, N3P3CI6 (HCCP), serves as the main inorganic template to produce organocyclotriphosphazenes. Herein, initially, diamines (1-6) were synthesized, which were used as ligands to obtain tetrachlorospirocyclotriphosphazenes (1a-6a). Geminal dichloro (7-9) and fully substituted (10-13) N-ferrocenyl-N′-(4-chlorobenzyl)spiro-(NN)-cyclotriphosphazenes were obtained from the reactions of tetrachlorophosphazenes (5a and 6a) with pyrrolidine and 1,4-dioxa-8-aza-spiro [4,5]decane (DASD). Geminal phosphazenes (7-9) have “chiral P atoms”. The 31P-spectrum of 9 with the addition of chiral solvating agent (CSA), (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol, proved that this compound exists as a “racemate.” The structural characterizations of the new phosphazenes were carried out using 1D NMR (1H, 13C, 31P) and LC-MS techniques. Single-crystal X-ray crystallography revealed the molecular and crystal structures of tetrachloro (5a and 6a) and tetra-pyrrolidino (10) cyclotriphosphazenes. Moreover, the highest free radical scavenging activities (FRSAs, %) were observed for 8 (21.8 ± 0.6). In addition, interactions with DNA and enzyme digestions were investigated. Also, the antibacterial and antifungal activities of all compounds were evaluated and compared with various cyclotriphosphazenes containing ferrocenyl/4-chlorobenzyl pendant arms for the structure-activity relationship (SAR) using MIC, MBC and MFC values. Dichlorophosphazene 8 (MIC = 9.8 μM) is very effective against B. cereus, B. subtilis, S. aureus, E. faecalis and E. hirae bacteria. However, fully-substituted phosphazene 10 (MIC = 9.8 μM) exhibits potent antifungal activity against C. albicans and C. krusei. These distinctions highlight their potential for specific bacterial and fungal threats.