Facile synthesis and antifungal evaluation of hypervalent organoantimony(iii) and organobismuth(iii) thioates with tridentate C,N,C-coordinating ligands

Abstract

In the present work, a series of organometallic thioates bearing a 5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine or -azabismocine framework were synthesized through the cross-coupling reactions of the corresponding halide precursors with thiols and disulfides at room temperature. The former transformation can be achieved under additive-free conditions, and mild dithiothreitol (DTT) is the only additive in the latter. Both methods feature simple operation, a broad substrate scope, and good reaction yields. Antifungal assays showed that the synthesized organobismuth(III) thioates possess significantly higher antibiotic activity against Candida albicans than clinical fluconazole, while the inhibitory effects of Sb-sulfenylated products are low to negligible. Furthermore, the antibiofilm potential of such Bi–S bond-containing compounds was discovered as well.