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 Jul 26;16(8):6271-305. doi: 10.3390/molecules16086271.

Abstract

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.

MeSH terms

  • Acetamides / chemical synthesis*
  • Ampicillin / pharmacology
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Bacillus cereus / drug effects
  • Bacillus cereus / growth & development
  • Bacillus subtilis / drug effects
  • Bacillus subtilis / growth & development
  • Candida albicans / drug effects
  • Candida albicans / growth & development
  • Coloring Agents / chemical synthesis
  • Coloring Agents / pharmacology*
  • Drug Design
  • Escherichia coli / drug effects
  • Escherichia coli / growth & development
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Materials Testing
  • Microbial Sensitivity Tests
  • Nitriles / chemistry
  • Prodrugs / chemical synthesis
  • Prodrugs / pharmacology*
  • Pyrazoles / chemistry
  • Pyrimidines / chemistry
  • Textile Industry
  • Textiles
  • Thiazoles / chemistry
  • Thiophenes / chemical synthesis*

Substances

  • Acetamides
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Coloring Agents
  • Heterocyclic Compounds, 2-Ring
  • Nitriles
  • Prodrugs
  • Pyrazoles
  • Pyrimidines
  • Thiazoles
  • Thiophenes
  • enaminonitrile
  • pyrazole
  • Ampicillin