Chiral self-assembly of triorganotin complexes: Syntheses, characterization, crystal structures and antitumor activity of organotin(IV) complexes containing (R)-(+)-methylsuccinic acid, (S)-(+)-methylglutaric acid and L-(-)-malic acid ligands

Six new chiral triorganotin(IV) complexes, {(R3Sn)(2)[C3H6(COO)(2)]}(n), (R = Me: 1; Bu: 2), ((R3Sn)(2)[C4H8 (COO)(2)]}(n) (R = Me: 3; Bu: 4), and {{R3Sn)(2)[C2H4O(COO)(2)]}(n) (R = Me: 5; Bu: 6) have been prepared by treatment of (R)(+)-methylsuccinic acid, (S)-(+)-methylglutaric acid and L-(-)-malic acid, with the corresponding R3SnCl (R = Me, Bu) and sodium ethoxide in methanol. All the complexes were characterized by elemental analysis, FT-IR, NMR(H-1, C-13, Sn-119) spectroscopy and TGA. Except for 3, all of the complexes were also characterized by X-ray crystallography. The structural analyses reveal that complexes 1 and Shave 2D network structures in which (R)-(+)-methylsuccinic acid and L-(-)-malic acid act as tetradentate ligands coordinated to trimethyltin(IV) ions. Complexes 2 and 4 have 3D metal-organic framework structures in which the deprotoned acids serve as tetradentate ligands. Complex 6 adopts a 1D zigzag chain structure and forms a 2D supramolecular framework through intermolecular C-H center dot center dot center dot O interactions. In addition, the antitumor activities of complexes 1-6 have been studied. We also have measured the specific rotation of the chiral dicarboxylic acids and the organotin derivatives. (C) 2011 Elsevier Ltd. All rights reserved.