Cu, Pt, and Pd complexes of the 3-deoxy-1,2-bis(thiosemicarbazone) derivedfrom D-glucose

3-Deoxy-D-erythro-hexos-2-ulose bis(thiosemicarbazone) (1) acts as a tetrad entate ligand of the N2S2 type which forms stable coordination complexes wi th metal(II) cations. The Cu(II), Pt(II), and Pd(II) chelates (2, 4, and 6, respectively) of 1 were synthesized and characterized by elemental analysi s and NMR spectroscopy. The NMR spectra of the Pt complex (4) showed the co upling of H-l and C-l, C-2 of the bis(thiosemicarbazone) with Pt-195 (33.7% naturally occurring), which supports the structure proposed for the chelat e. The complexes 2, 4, and 6 were acetylated to give the corresponding tri- O-acetyl derivatives 3, 5, and 7. Elimination of Cu(II) from 3 with hydroge n sulfide afforded 8, the tri-O-acetyl derivative of 1. Preliminary studies have shown antiviral activity of chelates 2, 4, and 6 against poliovirus t ype 1. (C) 2000 Elsevier Science Ltd. All rights reserved.