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

Design, Synthesis, and Antibacterial Activity of Spiropyrimidinone Derivatives Incorporated Azo... 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%). http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Fibers and Polymers Springer Journals

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

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Publisher
Springer Journals
Copyright
Copyright © The Korean Fiber Society 2022
ISSN
1229-9197
eISSN
1875-0052
DOI
10.1007/s12221-022-4032-4
Publisher site
See Article on Publisher Site

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%).

Journal

Fibers and PolymersSpringer Journals

Published: Aug 1, 2022

Keywords: Spiropyrimidine; Azo-disperse dyes; Sulfonamide; Polyester printing; Antibacterial

References