Regioselective Ring-Opening of Epoxide and N-Tosylaziridine with 4-Hydroxydithiocoumarin: Key Precursors for 2,3-Dihydro-1,4-oxathiin and 2,3-Dihydro-1,4-thiazine Derivatives

Regioselective ring-opening reaction between 4-hydroxydithiocoumarins with various epoxides and N-tosylaziridines is achieved for the synthesis of beta-hydroxysulfides and beta-N-tosylaminosulfides. The present protocols showed high regioselectivity, broad substrates scope compatibility, and mild reaction conditions. In addition, some of the ring-opening products are utilized for the conversion of 2,3-dihydro-1,4-oxathiin and 2,3-dihydro-1,4-thiazine derivatives in presence of 10 mol% Culin DMF at 120 C. Moreover, the antiproliferative activity study of the newly synthesized compounds, namely beta-hydroxysulfides (3d, 3i & 3m) and beta-aminosulfides (5a & 5e), have been investigated. Furthermore, flow cytometry analysis-based measurements of elevated reactive oxygen species (ROS) upon treatment of MCF-7 and HeLa cells with 3d, 3i, and 3m are commensurate with their anti-cancer properties.

Automated summary

Regioselective ring-opening reactions were successfully used for the synthesis of beta-hydroxysulfides and beta-N-tosylaminosulfides, showing high selectivity, broad substrate compatibility, and mild reaction conditions. The newly synthesized compounds exhibited antiproliferative activity and anti-cancer properties.