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Structure of azo dye organotin(IV) compounds containing a C,N‐chelating ligand, part II, and their in vitro antifungal activity
Author(s) -
Novák Petr,
Lyčka Antonín,
Císařová Ivana,
Buchta Vladimír,
Silva Luís,
Kolářová Lenka,
Růžička Aleš,
Holeček Jaroslav
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.845
Subject(s) - chemistry , trigonal bipyramidal molecular geometry , moiety , tin , tautomer , electrospray ionization , chloroform , chelation , intramolecular force , antifungal , ligand (biochemistry) , stereochemistry , medicinal chemistry , proton nmr , hydrazone , mass spectrometry , crystallography , crystal structure , organic chemistry , medicine , biochemistry , receptor , chromatography , dermatology
Eight complexes of azo dyes used in routine industrial processes and the [(2‐dimethylaminomethyl) phenyl](R 2 )tin(IV) moiety (R = Ph or n ‐Bu) have been prepared, their NMR, electrospray ionization mass spectrometry, IR and UV–VIS spectra measured, and the X‐ray structure of {[2‐( N , N ‐dimethylaminomethyl)phenyl](diphenyl)}tin(IV)‐2‐{[ N ′‐(2‐oxo‐1‐phenylcarbamoylpropyliden)hydrazo]}benzoate ( 3a ), determined. The compounds reveal similar structures in chloroform solution (NMR) and in the solid state (X‐ray, IR). Four compounds exist in the hydrazone tautomeric form. The central tin atoms in all compounds exist in slightly distorted trans ‐trigonal bipyramidal geometry with the ‘negative’ atoms (nitrogen, oxygen) in axial and the carbon atoms in equatorial positions; no intramolecular attacks from the dyes' cores were observed. The in vitro antifungal activity of the compounds studied was comparable to similar organotin(IV) compounds and antifungal drugs in clinical use. Copyright © 2005 John Wiley & Sons, Ltd.