Synthesis and characterization of new cyclotriphosphazene compounds

被引：38
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
收藏
页码：1454 / 1461
页数：8
相关论文
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
    ALLCOCK, HR
    DIEFENBACH, U
    PUCHER, SR
    [J]. INORGANIC CHEMISTRY, 1994, 33 (14) : 3091 - 3095
  • [3] REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN SUBSTITUTION-REACTIONS OF CYCLOPHOSPHAZENES
    ALLEN, CW
    [J]. 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
    Asmafiliz, Nuran
    Kilic, Zeynel
    Ozturk, Asli
    Hokelek, Tuncer
    Koc, L. Yasemin
    Acik, Leyla
    Kisa, Ozgul
    Albay, Ali
    Ustundag, Zafer
    Solak, Ali Osman
    [J]. INORGANIC CHEMISTRY, 2009, 48 (21) : 10102 - 10116
  • [6] Columnar mesomorphic organizations in cyclotriphosphazenes
    Barberá, J
    Bardají, M
    Jiménez, J
    Laguna, A
    Martínez, MP
    Oriol, L
    Serrano, JL
    Zaragozano, I
    [J]. 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
    Besli, S
    Coles, SJ
    Davies, DB
    Eaton, RJ
    Kiliç, A
    Shaw, RA
    [J]. 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
    Besli, S
    Coles, SJ
    Davies, DB
    Eaton, RJ
    Hursthouse, MB
    Kiliç, A
    Shaw, RA
    Çiftçi, GY
    Yesilot, S
    [J]. 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
    Besli, S
    Coles, SJ
    Davies, DB
    Hursthouse, MB
    Kiliç, A
    Mayer, TA
    Shaw, RA
    Uslu, A
    [J]. 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
    Besli, Serap
    Coles, Simon J.
    Davarci, Derya
    Davies, David B.
    Yuksel, Fatma
    [J]. POLYHEDRON, 2011, 30 (02) : 329 - 339
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