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

AKBAŞ, HÜSEYİN; ŞENOCAK, AYŞEGÜL; Kılıç, Zeynel; ERDEN TAYHAN, SEÇİL; BİLGİN, SEMA; Yıldırım, Aslı; Hökelek, Tuncer

doi:10.1016/j.molstruc.2023.135209

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

Yazarlar (7)

Prof. 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	Diğer (Teknik, not, yorum, vaka takdimi, editöre mektup, özet, kitap krıtiği, araştırma notu, bilirkişi raporu ve benzeri) (SCI, SSCI, AHCI, SCI-Exp dergilerinde yayınlanan teknik not, editöre mektup, tartışma, vaka takdimi ve özet türünden makale)
Dergi Adı	Journal of Molecular Structure (Q2)
Dergi ISSN	0022-2860 Dergi Bilgileri (2023)
Makale Dili	İngilizce	Basım Tarihi	06-2023
Cilt / Sayı / Sayfa	1282 / 1 / –	DOI	10.1016/j.molstruc.2023.135209
UAK Araştırma Alanları

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

Antimigratory acitivity | Antiproliferative activity | Cyclotriphosphazenes | Furan | Spectroscopy

Science Direct

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
Scopus	18

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

Dergi Adı	Journal of Molecular Structure
Kısa Adı	J MOL STRUCT
Yayıncı	ELSEVIER
Açık Erişim	Hayır
ISSN	0022-2860
E-ISSN	1872-8014
Wos Quartile	Q2
Scopus Quartile	Q2
Tarandığı Indeksler	SCIE , Scopus
WoS Kategoriler	CHEMISTRY, PHYSICAL
Scopus Kategoriler	ANALYTICAL CHEMISTRY \| INORGANIC CHEMISTRY \| ORGANIC CHEMISTRY \| SPECTROSCOPY