Cyclic phosphazenes have an important role in biological activity studies, drug design, pharmacology and toxicology as well as determination of their chemical, physical, crystallographic and spectroscopic properties. Due to its spatial orientation and considerably reactive P-Cl bonds, hexachlorocyclotriphosphazene (N3P3Cl6; trimer; HCCP) is appropriate ring for nucleophilic substitution reactions. Thus, trimer can be functionalized with different substituents and gain different properties according to substituents. So, trimer has been used as starting molecule to synthesize these hybrid compounds. One of the pharmacologically active compounds is carbazole. It is known that carbazole derivatives have antioxidant, antibacterial, antitumor properties. In this study, the unsymmetrically substituted dispirocyclotriphosphazenes were synthesized. These compounds represent the first examples of the cis/trans unsymmetric dispiro cyclotriphosphazenes with (N/N donor atoms) bulky side groups. Firstly, benzyldiamines (1 and 2) have been synthesized from reactions of benzaldehyde with N-methylethylenediamine and N-ethylethylenediamine. On the other hand, from the reaction of 9-methyl-3-carbazole-carboxaldehyde with N-methylethylenediamine, carbazolyldiamine (5) with N/N donor atoms has been obtained. Besides, mono(benzyldiamino)spirocyclotriphosphazenes (3 and 4) synthesized from reactions of trimer and benzyldiamines. Then, cis/trans-dispirophosphazenes (6-9) obtained as a result of reactions of the tetrachloro monospirocyclotriphosphazenes with carbazolyldiamine with conventional methods at 1: 1 stoichiometric ratio. Structures of dispirophosphazenes containing carbazole unit enlightened with spectroscopic methods. Structure of 8 has been characterized using X-ray crystallography technique. Compounds were screened for antimicrobial and antifungal activity against G(+) and G(−) bacteria, and fungi. In addition, the interactions of synthesized phosphazenes with plasmid DNA were investigated.

Unsymmetrically substituted dispirocyclotriphosphazenes: Synthesis, spectroscopy, crystallography and biological activity studies

ACS Spring 2022

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