Synthesis, Characterization and Biological Activity of Diorganotin(IV) Complexes of N‐(3,5‐Dibromo‐salicylidene)‐ α‐amino Acid

The diorganotin(IV) complexes of N-(3,5-dibromosalicylidene)-α-amino acid, R′2Sn(2-O-3,5-Br2C6H2CHNCHRCOO)(where R=H, Me, i-Pr, Bz; R′ =n-Bu, Cy), were synthesized by the reactions of diorganotin dichlorides with in situ formed potassium salt of N-(3,5-dibromosalicylidene)-α-amino acid and characterized by elemental analysis, IR and NMR (1H, 13C and 119Sn) spectra. The crystal structures of n-Bu2Sn(2-O-3,5-Br2C6H2CHNCHRCOO)(R=i-Pr, Bz) and Cy2Sn(2-O-3,5-Br2C6H2CHNCHRCOO)(R=Me, Bz) were determined by X-ray single crystal diffraction and showed that the tin atoms are in a distorted trigonal bipyramidal geometry to form five- and six-membered chelate rings with the tridentate ligand. Bioassay results indicated that the compounds possess better in vitro antitumour activity against three human tumour cell lines, HeLa, CoLo205 and MCF-7, than cis-platin and moderate anti-bacterial activity against two bacteria, E. coli and S. aureus.

[1]  Philip Smith,et al.  Group IV organometallic compounds. : IX. Preparation and spectroscopic studies of complexes of bis(β-carbomethoxyethyl)tin dichloride , 1981 .

[2]  S. Leppard,et al.  Synthesis and Characterization of New Chiral Schiff Base Complexes with Diiminobinaphthyl or Diiminocyclohexyl Moieties as Potential Enantioselective Epoxidation Catalysts. , 1996, Inorganic chemistry.

[3]  Herbert Höpfl,et al.  Self-assembly of diorganotin(IV) oxides (R = Me, nBu, Ph) and 2,5-pyridinedicarboxylic acid to polymeric and trinuclear macrocyclic hybrids with porous solid-state structures: influence of substituents and solvent on the supramolecular structure. , 2005, Journal of the American Chemical Society.

[4]  D. Vos,et al.  Synthesis, characteristic spectral studies and in vitro antimicrobial and antitumour activities of organotin(IV) complexes of Schiff bases derived from amino-acids , 1997 .

[5]  V. Baskar,et al.  Organotin assemblies containing SnO bonds , 2002 .

[6]  Keitaro Nakatani,et al.  Second-Harmonic Generation within the P212121 Space Group, in a Series of Chiral (Salicylaldiminato)tin Schiff Base Complexes , 2006 .

[7]  Norberto Farfán,et al.  One-step preparation, structural assignment, and X-ray study of 2,2-di-n-butyl- and 2,2-diphenyl-6-aza-1,3-dioxa-2-stannabenzocyclononen-4-ones derived from amino acids. , 2003, Chemistry.

[8]  M. Holčapek,et al.  Self-assembly of diorganotin(IV) 2-{((E)-1-(2-oxyaryl)alkylidene)amino}acetates: An investigation of structures by X-ray diffraction, solution and solid-state tin NMR, and electrospray ionization MS , 2005 .

[9]  H. Yin,et al.  Synthesis and structural characterization of diorganotin(IV) esters of salicylidene-amino acids , 2004 .

[10]  M. Biesemans,,et al.  Organotin compounds: from kinetics to stereochemistry and antitumour activities , 2005 .

[11]  Da-qi Wang,et al.  Self-assembly of dialkyltin moieties and mercaptobenzoic acid into macrocyclic complexes with hydrophobic "pseudo-cage" or double-cavity structures: supramolecular infrastructures involving intermolecular C-H...S weak hydrogen bonds and pi-pi interactions. , 2005, Chemistry.

[12]  J. J. Zuckerman,et al.  Trialkyltin derivatives of amino acids and dipeptides , 1973 .

[13]  M. Gielen.  Review: Organotin compounds and their therapeutic potential: a report from the Organometallic Chemistry Department of the Free University of Brussels , 2002 .

[14]  G. Koten,et al.  Novel chiral triorganotin halides. Stabilization of optically active tin centers by intramolecular coordination , 1976 .

[15]  Wang Chuan-hua,et al.  Synthesis, Characterization and Properties of Organotin Complexes Dibutyltin(IV) Bis(heteroaromatic carboxylate) and Crystal Structure of Dibutyltin(IV) Bis(2‐thiazolylcarboxylate) , 2005 .

[16]  Edward R. T. Tiekink,et al.  Synthesis, Characterization and X-ray Structures of Diphenyltin(IV) N-(2-Hydroxyacetophenone)glycinate, Its 1:1 Adduct with Triphenyltin(IV) Chloride, and Related Systems , 1998 .

[17]  Yu‐Xi Sun,et al.  Synthesis, characterization and biological activity of diphenyltin(IV) complexes of N‐(3,5‐dibromosalicylidene)‐α‐amino acid and their diphenyltin dichloride adducts , 2006 .

[18]  Huijun Li,et al.  Synthesis, structural characterization and cytotoxic activity of diorganotin(IV) complexes of N‐(5‐halosalicylidene)‐α‐amino acid , 2005 .