An intramolecular hydrogen bond-promoted "green" Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity

RSC Adv. 2022 Nov 21;12(51):33175-33179. doi: 10.1039/d2ra04958a. eCollection 2022 Nov 15.

Abstract

We report a "green chemistry"-based Ugi cascade reaction to furnish a series of 2,5-diketopiperazines (through nucleophilic attack of amides upon ketones in Ugi adducts) at moderate-to-good yields. Investigation with the MTT assay revealed compound (±) 5c to exhibit potent anticancer activities against acute myeloid leukaemia (MV411; IC50 = 1.7 μM) and acute T lymphocyte leukaemia (Jurkat; IC50 = 5.7 μM) cell lines.