Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, ¹H NMR, ¹³C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 μM) against HeLa cell line. IC₅₀ results also confirm these activities. The compounds 9, 10 and 11 have the IC₅₀ values of 1.10 μM, 1.51 μM and 1.02 μM, respectively while 5-FU has 2.51 μM. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.