Ferrocenyl pseudo-dipeptides derived from 1,2-O-isopropylidene-α-D-xylofuranose: Synthesis, electrochemistry and cytotoxicity evaluation

•First examples of Ferrocenyl peptides with isopropylidene protected sugar.•The electrochemical diffusion of the compounds dependent on the amino acid side chain.•Exhibited promising cytotoxic activity.

In this article, we describe the synthesis of a new series of ferrocene conjugates of pseudo-dipeptides derived from d-xylose and different l-amino acids. The pseudo-dipeptides (3a–f) were synthesized by the reaction of 5-amino-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (1) with different N-Boc-L-amino acids (2a–f). Subsequently, the pseudo-dipeptides were insitu converted to amino-amides (4a–f) and treated with ferrocenoyl chloride to obtain the ferrocenyl xylofuranose pseudo-dipeptide conjugates (5a–f). The structure of the pseudo-dipeptide 3b was determined by X-ray crystallography. Low electrochemical diffusion coefficient (Df) values were obtained for the ferrocenyl compounds (5a–f) in DMSO-buffer solutions. Promising cytotoxicity was observed for the ferrocenyl pseudo-dipeptides (5a–f) as compared to the parent pseudo-dipeptides (3a–f).

Graphical abstractIn this article we describe the synthesis of ferrocenyl pseudo-dipeptides derived from 1,2-O-isopropylidene-α-D-xylofuranose. The ferrocenyl pseudo-dipeptides have shown low diffusion coefficient values in DMSO-buffer solutions and promising cytotoxic activity against breast cancer cell lines.Figure optionsDownload full-size imageDownload as PowerPoint slide