Issue 3, 2018

Syntheses, spectroscopic and crystallographic characterizations of cis- and trans-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activities

Abstract

New cis- (4–6) and trans-dispirocyclic ferrocenylphosphazene derivatives (7–9) were obtained by reactions of hexachlorocyclotriphosphazene (N3P3Cl6) with N-alkyl-N-monoferrocenyldiamines of the formula FcCH2NH(CH2)nNHR [n = 2, R = CH3 (1); n = 2, R = C2H5 (2) and n = 3, R = CH3 (3)]. Characterizations of the products were performed using MS, FTIR, 1H, 13C and 31P NMR techniques. The crystal structures of 5 (with 8), 6, 7 and 9 were determined by X-ray crystallography. The most important result of this study was that the trans chiral phosphazenes crystallized as only one enantiomer. Studies of the antibacterial and antifungal activity of the phosphazenes (4–9) showed that compounds 6 and 7 were effective against P. vulgaris and K. pneumoniae. The cytotoxic activities of 4–9 against L929 fibroblasts and DLD-1 colon cancer cells were investigated. The necrotic effects of 4 and 7 were greater in the DLD-1 cell line than those in the L929 cell line. DFT calculations were carried out using the B3LYP functional with the LANL2DZ basis set to determine the energies, the orientations of the molecular orbitals (HOMOs and LUMOs) and the molecular electrostatic potential (MEP) surfaces of the partly substituted cyclotriphosphazenes (6, 7 and 9). The results for 6, 7 and 9 revealed that these bonded to the active sites of A-DNA and B-DNA by weak non-covalent interactions, which was also supported by molecular docking investigations.

Graphical abstract: Syntheses, spectroscopic and crystallographic characterizations of cis- and trans-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activities

Supplementary files

Article information

Article type
Paper
Submitted
22 Sep 2017
Accepted
16 Dec 2017
First published
18 Dec 2017

New J. Chem., 2018,42, 1740-1756

Syntheses, spectroscopic and crystallographic characterizations of cis- and trans-dispirocyclic ferrocenylphosphazenes: molecular dockings, cytotoxic and antimicrobial activities

Y. Tümer, N. Asmafiliz, C. T. Zeyrek, Z. Kılıç, L. Açık, S. P. Çelik, M. Türk, B. Çağdaş Tunalı, H. Ünver and T. Hökelek, New J. Chem., 2018, 42, 1740 DOI: 10.1039/C7NJ03643D

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