Design, Synthesis, and Antibacterial Activity of Spiropyrimidinone Derivatives Incorporated Azo Sulfonamide Chromophore for Polyester Printing Application

Abstract

We designed and developed a novel series of bioactive disperse dyes by conjugation of spirocyclic 2-thiopyrimidine scaffold with aryl or sulfa drug moieties in the same construct through azo linker to take advantage of the bioactive character of both motifs. The target molecules were simply approached on a gram scale via the diazocoupling of spirocyclic 2-thiouracil 1 with aryl diazonium chloride derivatives to afford the heterocyclic azo-disperse dyes 4a–e in excellent yield. These azo dyes were effectively utilized to make pastes for silkscreen printing of polyester fabrics. The color characteristics of the dyes and their fastness properties including washing, rubbing, perspiration, sublimation, and light fastness were also investigated. The antimicrobial activity of the produced dyes 4a–e was evaluated against some Gram-positive and Gram-negative bacteria, and the results revealed that 4d was more active than the standard drug cefoperazone against the Gram-positive bacteria S. aureus. The antibacterial efficacy of the treated fabrics has also been investigated revealing that the dyed fabric 4b was found to have a potent inhibition on B. cereus (93 %), and against E. coli with a reduction of (90%).