Synthesis, structural characterization, and cytotoxic activity of new spirocyclic octachlorocyclotetraphosphazenes

Isiklan M., Sayin L., Sonkaya O., HÖKELEK T., Turk M., Oguztuzun S.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.191, no.9, pp.1216-1222, 2016 (SCI-Expanded) identifier identifier


Octachlorocyclotetraphosphazene, N4P4Cl8, (1) was reacted with N, N-dibenzylethylenediamine to synthesize partially substituted monospiro- (2), dispiro- (5) and tetraspirocyclotetraphosphazene (8) derivatives. The reactions of 2 and 5 with excess pyrrolidine and morpholine produced fully substituted pyrrolidino (3 and 6) and morpholino (4 and 7) spirocyclotetraphosphazenes. The structures of the compounds were determined with 1D (H-1, C-13, P-31, and DEPT) NMR, 2D (HSQC) NMR, ESI-MS, FTIR, and elemental analysis. The solid-state structures of 6 and 7 were examined by X-ray crystallography. In 7, intramolecular C-H...O hydrogen bonds link the molecules into centrosymmetric dimmers. The cytotoxic activity of all the compounds against human cervix carcinoma cell lines (HeLa) was investigated. The study showed that these compounds exert limited cytotoxic, apoptotic and necrotic effects on HeLa cancer cell lines.