Abstract
The Cl replacement reactions of hexachlorocyclotriphosphazene (trimer; N 3 P 3 Cl 6 ) with sodium (N-benzyl)- aminopropanoxides (1 and 2) produced monospiro- (3 and 4), cis-, and trans-dispirocyclotriphosphazenes (13–16). The monospiro tetrakis-aminocyclotriphosphazenes (5–12) were obtained by the Cl substitutions of 3 and 4 with different secondary amines. The cis- (13 and 14) and trans-dispirophosphazenes (15 and 16) possessed 2 chiral P centers, and they were able to present meso and racemic forms, respectively. Moreover, the structures of compounds 5 and 14 were designated using X-ray data. The absolute configuration of compound 14 was found as SR in the solid state. Analytical and spectroscopic data of the phosphazenes were consistent with their suggested structures. Antimicrobial activities of the benzyl-pendant-armed cyclotriphosphazenes were scrutinized against G(+) and G(−) bacteria and yeast strains. The bacterium most affected by the synthesized compounds was Pseudomonas aeruginosa . Minimum inhibitory concentrations and minimal bacterial concentrations were in the range of 125–500 μM. Interactions between the phosphazenes (3–12 and 15) and plasmid DNA were studied with agarose gel electrophoresis. The phosphazene- DNA interaction studies of the cyclotriphosphazenes revealed that phosphazenes 3, 4, and 15 had a substantial effect on supercoiled DNA by cleavage of the double helix.
Highlights
Phosphazenes refer to phosphorus-nitrogen compounds that occur by the sequential bonding of atoms to each other [1,2]
The Cl exchange reactions of 1 equimolar amount of sodium (Nbenzyl)aminopropanoxides (1 and 2) with 1 equimolar amount of N 3 P 3 Cl 6 afforded the monospirophosphazenes with a benzyl pendant arm (3 and 4), according to the literature method
The results revealed that compounds 3, 6, 7, 8, 9, 11, 12, and 15 were effective in suppressing the microbial growth of pathogenic bacteria with variable potency [compound 3 was active against S. typhimurium G(–) and P. vulgaris G(–); compound 6 against S. aureus G(+) and P. aeruginosa G(–); compound 7 against P. aeruginosa G(–); compound 9
Summary
Phosphazenes refer to phosphorus-nitrogen compounds that occur by the sequential bonding of atoms to each other [1,2]. Hexachlorocyclotriphosphazene (N 3 P 3 Cl 6 , trimer) is versatile and has the ability to react with different mono-, di-, and multifunctional reagents [3,4,5]. When trimer is reacted with monofunctional agents, at least 6 different cyclotriphosphazene derivatives can be formed [6]. The Cl replacement reactions of trimer with one equimolar difunctional reagent may predominantly yield monospiro products when compared to other expected ansa- and bino-isomers [7,8]. When two equimolar difunctional agents are used, dispirocyclotriphosphazenes with cis- and trans-geometrical and meso/racemic optical isomers can occur [9,10,11]. It is difficult to separate these isomers from each other; very few optical and
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