Syntheses of tetrachloro and tetraamino(2-furanylmethyl)spiro(N/N) cyclotriphosphazenes: Chemical, structural elucidation, antiproliferative and antimigratory activity studies      
Yazarlar (7)
Doç. Dr. Hüseyin AKBAŞ Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Doç. Dr. Ayşegül ŞENOCAK Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Zeynel Kılıç
Ankara Üniversitesi, Türkiye
Doç. Dr. Seçil ERDEN TAYHAN Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Doç. Dr. Sema BİLGİN Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Aslı Yıldırım
Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Tuncer Hökelek
Hacettepe Üniversitesi, Türkiye
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale
Dergi Adı Journal of Molecular Structure
Dergi ISSN 0022-2860 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI-Expanded
Dergi Grubu Q2
Makale Dili İngilizce
Basım Tarihi 06-2023
Cilt No 1282
Sayı 1
DOI Numarası 10.1016/j.molstruc.2023.135209
Makale Linki http://dx.doi.org/10.1016/j.molstruc.2023.135209
Özet
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).
Anahtar Kelimeler
Cyclotriphosphazenes | Spectroscopy | Furan | Antiproliferative activity | Antimigratory acitivity