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).

In 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 as PowerPoint slide