The pharmacological effects of carbon to silicon bioisosteric replacements have been widely explored in drug design and medicinal chemistry. Here, we present a systematic investigation of the impact of different silyl groups on the anticancer activity of mucobromic acid (MBA) bearing furan-2(5H)-one core. We describe a comprehensive characterization of obtained compounds with respect to their anticancer potency and selectivity towards cancer cells. All four novel compounds exert stronger antiproliferative activity than MBA. Moreover, 3b induce apoptosis in colon cancer cell lines. A detailed investigation of the mechanism of action revealed that 3b activity stems from the down-regulation of survivin and the activation of caspase-3. Furthermore, compound 3b attenuates the clonogenic potential of HCT-116 cells. Interestingly, we also found that depending on the type of the silyl group, compound selectivity towards cancer cells could be precisely controlled. Collectively, we demonstrated the utility of silyl groups for adjusting both the potency and selectivity of silicon-containing compounds. These data reveal a link between the types of silyl group and compound potency, which could have bearings for the design of novel silicon-based anticancer drugs.

3,4-Dichloro-5-hydroxy-2(5H)-furanone and its dibromo analog are highly reactive molecules. Both are members of the 2(5H)-furanone family, which are important as pharmacophores present in drugs and natural products. Compounds possessing the 2(5H)-furanone skeleton isolated from plants and marine organisms exhibit bioactivity against various microorganisms and viruses and can also be used in other medical treatments. The structures of these 3,4-dihalo-2(5H)-furanones cause their high reactivity due to the presence of a carbonyl group on the C2 carbon conjugated with a double bond and a hydroxyl group on the C5 carbon. Two labile halogen atoms on carbons 3 and 4 offer additional possibilities for the introduction of other substituents. These structural features make 3,4-dihalo-5-hydroxy-2(5H)-furanones versatile reactants in chemical synthesis. In this review, we present methods of 3,4-dihalo-5-hydroxy-2(5H)-furanone synthesis, their applications as substrates in various chemical transformations, and examples of their biologically active derivatives.

A series of glycoconjugates, derivatives of genistein containing a C-glycosylated carbohydrate moiety, were synthesized and their anticancer activity was tested in vitro in the human cell lines HCT 116 and DU 145. The target compounds 15–17 were synthesized by treating ω-bromoalkyl C-glycosides derived from L-rhamnal (1) with a tetrabutylammonium salt of genistein. The new, metabolically stable analogs of previously studied O-glycosidic genistein derivatives inhibited proliferation of cancer cell lines through inhibition of the cell cycle.