Syntheses of tetrachloro and tetraamino(2-furanylmethyl)spiro(N/N) cyclotriphosphazenes: Chemical, structural elucidation, antiproliferative and antimigratory activity studies


Akbaş H., Şenocak A., Kılıç Z., Tayhan S. E., Bilgin S., Yıldırım A., ...More

Journal of Molecular Structure, vol.1282, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Review
  • Volume: 1282
  • Publication Date: 2023
  • Doi Number: 10.1016/j.molstruc.2023.135209
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Cyclotriphosphazenes, Spectroscopy, Furan, Antiproliferative activity, Antimigratory acitivity
  • Hacettepe University Affiliated: Yes

Abstract

In this research, the Schiff bases prepared from the condensation reactions of furfural with N-ethyl-1,2-diaminoethane and N-methyl-1,3-diaminopropane were reduced to N/N-donor type diamines (1 and 2) to obtain the starting diamines. The tetrachloro(2-furanylmethyl)spiro-(N/N)cyclotriphosphazenes (3 and 4) were formed regioselectively in excellent yields, when the hexachlorocyclotriphosphazene, N3P3Cl6 (HCCP, trimer), was reacted with the diamines. The Cl replacement reactions of 3 and 4 with pyrrolidine and piperidine yielded tetrapyrrolidino (3a and 4a) and tetrapiperidino (3b and 4b) cyclotriphosphazenes, respectively. The structures of all cyclotriphosphazenes were proven by FT-IR, HRMS, 1H, 13C, and 31P NMR data. The crystal structures of 3, 4, 3a, 3b and 4b were elucidated using single crystal X-ray crystallography. Tetraamino(2-furanylmethyl)spiro(N/N)cyclotriphosphazenes (3a, 3b, 4a and 4b) were tested by MTT assay for their ability to inhibit the growth of human breast cancer MCF-7, prostate cancer PC-3 and colon cancer HT-29 cells. Besides, the antimigratory activities of these compounds on three cell lines were also investigated by in vitro scratch analysis. The results show that the compounds have varying degrees of success in inhibiting the growth and migration of various cancer cells. However, the most effective phosphazene derivatives against these cancer cell lines were the five-membered N-ethyl phosphazenes (3a and 3b).