Cerium(IV)‐Catalyzed Allylic Oxidation of 3‐Sulfolene: An Efficient Tool for the Synthesis of 4‐Substituted Sulfol‐2‐Enes with Antiproliferative Activity

• DOI: 10.1002/cmdc.202500010
• Publication Date: 2025-02-26T03:36:00Z
• Authors: Elżbieta Łastawiecka; Magdalena Mizersk...; Adrianna Sławińsk...; Karolina Mrozik; Barbara Zdzisińska
• Keywords: Synthon

Cyclic sulfones play an important role in the field of drug discovery and design due to their valuable properties broad range applications. Herein, we report efficient cerium(IV)-catalyzed allylic oxidation a simple 3-sulfolene. This process provides straightforward facile approach sulfol-2-en-4-one, versatile synthetic intermediate. Notably, this study represents first instance cerium catalysis employed oxidation. Furthermore, demonstrated transformation sulfol-2-en-4-one into 4-substituted sulfol-2-enes with therapeutic In silico analysis performed using SwissAdme tool indicated that obtained 4-amine (7a - 7d) 4-carbamate (9a 9b) derivatives met rules imposed on small-molecule drugs. Moreover, these compounds inhibited proliferation (MTT assay) colon cancer osteosarcoma cells. 7b 7c, which exhibited best selectivity index (ratio IC50 calculated for normal cells), induced cell cycle arrest apoptosis (flow cytometry analysis). Considering present results, cerium-catalyzed sulfol-3-ene proves be practical method synthesizing chemical synthon developing sulfolane derivatives, including those promising anticancer potential.