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Bismuth(III) saccharinate and thiosaccharinate complexes and the effect of ligand substitution on their activity against helicobacter pylori

Five bismuth(III) saccharinate and thiosaccharinate complexes, [Ph 2Bi(sac)]?1, [Bi(sac)3]n2, [Ph2Bi(tsac)]?4, [PhBi(tsac)2] n5, [Bi(tsac)3]n6 (sacH = saccharin, tsacH = thiosaccharin), have been synthesized and fully characterized. The tendency for ligand redistribution in [Ph2Bi(sac)]? has been investigated in solution by NMR spectroscopy. The structures of [Ph 2Bi(sac)]?1 and [Ph2Bi(tsac)] ?4 have been confirmed by X-ray crystallography. In Ph 2Bi(sac) the sac ligand is bound to a four-coordinate bismuth center via its imino nitrogen atom with an accompanying long-range Bi-O interaction. However, in the structure of [Ph2Bi(tsac)]? the ligand is sigma-bound through the exocyclic sulfur atom, giving a thiolate complex, confirming the more thiophilic nature of bismuth(III). Both complexes consist of polymeric chain structures with formally four-coordinated bismuth atoms. The complexes were assessed for their activity against H. pylori. The activity is both ligand dependent and sensitive to the degree of ligand substitution. The saccharinate complexes, 1 and 2, show activity comparable with standard tris-carboxylato bismuth(III) compounds, 6.25 mug/mL, while the activity of the thiolato complexes, 4-6, increases dramatically on increasing the number of thiolate groups from one to three (range 50-6.25 mug/mL). Saccharin, thiosaccharin, and BiPh3 were found to be inactive.

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Reference£º
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com