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Synthesis, Characterization and Antitumor Activity of 4-Ferrocenylpyridine-3, 5-Dicarbonitrile Derivatives and Sodium Polymeric Complexes Containing Carbanionic Ligands

Published online by Cambridge University Press:  11 May 2015

E. Klimova ,
J. Sánchez ,
M. Flores ,
S. Cortez ,
T. Ramírez ,
A. Churakov  and
M. Martínez
E. Klimova
Affiliation:
Facultad de Química, UNAM, México D. F.,C.P.04500, México, E- mail: [email protected]
J. Sánchez
Affiliation:
Facultad de Química, UNAM, México D. F.,C.P.04500, México, E- mail: [email protected]
M. Flores
Affiliation:
Facultad de Química, UNAM, México D. F.,C.P.04500, México, E- mail: [email protected]
S. Cortez
Affiliation:
Facultad de Química, UNAM, México D. F.,C.P.04500, México, E- mail: [email protected]
T. Ramírez
Affiliation:
Instituto de Química, UNAM, México D. F.,C.P.04500, México.
A. Churakov
Affiliation:
Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp., 31, Moscow 119991, Russia.
M. Martínez
Affiliation:
Instituto de Química, UNAM, México D. F.,C.P.04500, México.
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Abstract

The reactions of 2-cyano-3-ferrocenylacrylonitrile with malononitrile in a ROH/H2O medium in the presence of Na2CO3 afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles, 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenyl-methyl-3,4-dihydropyridine-3,5-dicarbonitriles and Na+ polymeric complexes: {[Na+(2-ferrocenyl(tetracyano)propenyl)−L]∞ and [Na+(2-amino-3,5-dicyano-4-ferrocenyl-6-pyridyl-dicyanomethyl)−L]∞ where L = ethanol, methanol. Complexes with L = acetonitrile (c), dimethylformamide (d), acetone (e), ethyl acetate (f) were prepared by recrystallization. The structures of the compounds 4b and Na+ polymeric complexes 5c and 6d, e were established by the spectroscopic data and X-ray diffraction analysis. Two compounds 3a and 4a were tested in vitro against six human tumor cell lines U-251, PC-3, K-562, HCT-15, MCF-7 and SKLU-1 to assess their in vitro antitumor activity. The results suggest biological specificity towards PC-3, K-562 and HCT-15 cells for compound 3a, and towards PC-3 cell for compound 4a at doses 50 μM, which are lower than Cisplatin IC50′s in the three cell lines.

Keywords

X-ray diffractionPolymerChemical reactionOrganicH.
Type
Articles
Information
MRS Online Proceedings Library (OPL) , Volume 1766: Symposium 5B – Structural and Chemical Characterization of Metals, Alloys, and Compounds—2014 , 2015 , pp. 9 - 17
Copyright
Copyright © Materials Research Society 2015 

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