Synthesis and characterization of new cyclotriphosphazene compounds

被引：40

作者：

Ciftci, Gonul Yenilmez ^{[1
]}

Ecik, Esra Tannverdi ^{[1
]}

Yildirim, Tuba ^{[2
]}

Bilgin, Kemal ^{[3
]}

Senkuytu, Elif ^{[1
]}

Yuksel, Fatma ^{[1
]}

Uludag, Yildiz ^{[4
]}

Kilic, Adem ^{[1
]}

机构：

[1] Gebze Inst Technol, Dept Chem, TR-41400 Gebze, Turkey

[2] Amasya Univ, Dept Biol, Fac Arts & Sci, TR-05100 Amasya, Turkey

[3] Ondokuz Mayis Univ, Dept Med Serv & Tech, Vocat Higher Sch Hlth Serv, TR-55139 Samsun, Turkey

[4] UEKAE Sci & Technol Res Council Turkey TUBITAK, TR-41470 Gebze, Turkey

来源：

TETRAHEDRON | 2013年 / 69卷 / 05期

关键词：

Cyclotriphosphazene; Spermine derivatives; Biological activity; Cytotoxic activity; PHOSPHORUS-NITROGEN COMPOUNDS; STRUCTURAL INVESTIGATIONS; SPERMINE DERIVATIVES; STEREOGENIC CENTERS; MOLECULAR-STRUCTURE; SPIRO; ANSA; CYCLOPHOSPHAZENES; CRYSTAL; HEXACHLOROCYCLOTRIPHOSPHAZATRIENE;

D O I：

10.1016/j.tet.2012.12.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the present study, Spiro (1a), dispiro (1b, 2, 3), per-substituted spermine-bridged (6-9) and dispiroansa spermine (10) derivatives of cyclotriphosphazene have been synthesized. The structures of the novel compounds (1b, 6-10) have been characterized by elemental analysis, FTIR, mass spectrometry, H-1 and P-31 NMR spectroscopy. The molecular structures of 1b, 2, 8, and 10 were determined by single crystal X-ray crystallography. In order to investigate the anti-tumour properties of the newly synthesized cyclotriphosphazene derivatives, in vitro cytotoxic activity test (MTT assay) has been performed using HT-29 (human colon adenocarcinoma) and Hep2 (human epidermoid larynx carcinoma) cell lines. The result of the MU assay showed that while compound 1a has cytotoxic effect on both Hep2 and HT-29 cell lines, compound 3 has only cytotoxic effect towards the Hep 2 cells. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1454 / 1461

页数：8

共 46 条

[1]

ALKUBAISI AH, 1989, HETEROCYCLES, V28, P347

[2] NEW MONOSPIROCYCLOTRIPHOSPHAZENES AND TRISPIROCYCLOTRIPHOSPHAZENES FROM THE REACTIONS OF (NPCL2)3 WITH AROMATIC ORTHO DINUCLEOPHILES [J].

ALLCOCK, HR ;

DIEFENBACH, U ;

PUCHER, SR .

INORGANIC CHEMISTRY, 1994, 33 (14) :3091-3095

[3] REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN SUBSTITUTION-REACTIONS OF CYCLOPHOSPHAZENES [J].

ALLEN, CW .

CHEMICAL REVIEWS, 1991, 91 (02) :119-135

[4]

[Anonymous], 2005, SADABS

[5] Phosphorus-Nitrogen Compounds. 18. Syntheses, Stereogenic Properties, Structural and Electrochemical Investigations, Biological Activities, and DNA Interactions of New Spirocyclic Mono- and Bisferrocenylphosphazene Derivatives [J].

Asmafiliz, Nuran ;

Kilic, Zeynel ;

Ozturk, Asli ;

Hokelek, Tuncer ;

Koc, L. Yasemin ;

Acik, Leyla ;

Kisa, Ozgul ;

Albay, Ali ;

Ustundag, Zafer ;

Solak, Ali Osman .

INORGANIC CHEMISTRY, 2009, 48 (21) :10102-10116

[6] Columnar mesomorphic organizations in cyclotriphosphazenes [J].

Barberá, J ;

Bardají, M ;

Jiménez, J ;

Laguna, A ;

Martínez, MP ;

Oriol, L ;

Serrano, JL ;

Zaragozano, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8994-9002

[7] Competitive formation of spiro and ansa derivatives in the reactions of tetrafluorobutane-1,4-diol with hexachlorocyclotriphosphazene:: A comparison with butane-1,4-diol [J].

Besli, S ;

Coles, SJ ;

Davies, DB ;

Eaton, RJ ;

Kiliç, A ;

Shaw, RA .

POLYHEDRON, 2006, 25 (04) :963-974

[8] Anomalous NMR behavior of meso compounds with remote stereogenic centers on addition of chiral shift reagent or chiral solvating agent [J].

Besli, S ;

Coles, SJ ;

Davies, DB ;

Eaton, RJ ;

Hursthouse, MB ;

Kiliç, A ;

Shaw, RA ;

Çiftçi, GY ;

Yesilot, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) :4943-4950

[9] Structural investigations of phosphorus-nitrogen compounds.: 4.: Steric and electronic effects in dibenzylamino derivatives of hexachlorocyclotriphosphazatriene and 4,4,6,6-tetrachloro-2,2-diphenylcyclotriphosphazatriene [J].

Besli, S ;

Coles, SJ ;

Davies, DB ;

Hursthouse, MB ;

Kiliç, A ;

Mayer, TA ;

Shaw, RA ;

Uslu, A .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 :545-552

[10] Effect of chain length on the formation of intramolecular and intermolecular products: Reaction of diols with cyclotriphosphazene [J].

Besli, Serap ;

Coles, Simon J. ;

Davarci, Derya ;

Davies, David B. ;

Yuksel, Fatma .

POLYHEDRON, 2011, 30 (02) :329-339

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