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Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems

1
Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan, Cairo, P.O. 11790, Egypt
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Department of Organic Chemistry, Faculty of Pharmacy, October University for Modern Sciences and Arts, October City, P.O. 12613, Egypt
3
Department of Chemistry, Faculty of Science, Cairo University, Giza, P.O. 12311, Egypt
*
Author to whom correspondence should be addressed.
Molecules 2011, 16(8), 6271-6305; https://doi.org/10.3390/molecules16086271
Received: 22 May 2011 / Revised: 4 July 2011 / Accepted: 4 July 2011 / Published: 26 July 2011
A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide or 2-phenylcarbamoyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide systems as precursors. The latter compounds were used to synthesize polyfunctional thiophene-, thiazole-, pyrazole, pyridine-, pyrimidine-, oxazine-, as well as acyclic moieties. The dyes and dye precursors were characterized by elemental analysis and spectral methods. All dyes and their precursors were screened in vitro and evaluated for both their antibacterial and antifungal activities. MIC data of the novel dye systems and their respective precursors showed significant antimicrobial activity against most tested organisms. Some compounds exhibited comparable or even higher efficiency than selected standards. Dyes were applied at 5% depth for disperse dyeing of nylon, acetate and polyester fabrics. Their spectral characteristics and fastness properties were measured and evaluated. View Full-Text
Keywords: heterocyclic; dyes; antimicrobial activity; textile finish; fastness heterocyclic; dyes; antimicrobial activity; textile finish; fastness
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Shams, H.Z.; Mohareb, R.M.; Helal, M.H.; Mahmoud, A.-S. Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems. Molecules 2011, 16, 6271-6305.

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