Synthesis of Thiazolopyrimidines via Annulation of N‐(4,6‐Diaryl‐2‐thioxo‐1,2,3,6‐tetrahydropyrimidin‐4‐yl)phenyl)aryl‐sulfonamides

Abstract

AbstractA series of 5,7‐diaryl‐5H‐thiazolo[3, 2‐a]pyrimidin‐3(2H)‐ones (4 a‐4 r) bearing sulfonamide scaffold have been synthesized by cyclocondensation of bromoacetic acid and N‐(4,6‐diaryl‐2‐thioxo‐1,2,3,6‐tetrahydropyrimidin‐4‐yl)phenyl)aryl‐sulfonamides (3 a‐3ab). Compounds 3 a‐3ab have been synthesized by cyclocondensation of sulfonamide chalcones (1) and thiourea. Acetic acid: acetate buffer system and temperature of the reaction system played an important role in conversion of 3 to 4. The synthesized compounds were evaluated for their in vitro anticancer activities against the strain of human breast cancer cell line MCF‐7. Compounds 3 e, 3 p, 4 h and 4 k with GI50 below 80 μM were found to be moderately cytotoxic against MCF‐7.