title: 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.
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.
authors.affiliation: Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan, Cairo, P.O. 11790, Egypt.
authors.forename: Hoda Zaki
authors.initials: HZ
authors.lastname: Shams
authors.forename: Rafat Milad
authors.initials: RM
authors.lastname: Mohareb
authors.forename: Maher Helmy
authors.initials: MH
authors.lastname: Helal
authors.forename: Amira El-Sayed
authors.initials: Ael-S
authors.lastname: Mahmoud
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis*; D000667:Ampicillin / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001409:Bacillus cereus / Q000187:drug effects / Q000254:growth & development; D001412:Bacillus subtilis / Q000187:drug effects / Q000254:growth & development; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D004396:Coloring Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D015195:Drug Design; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry; D008422:Materials Testing; D008826:Microbial Sensitivity Tests; D009570:Nitriles / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis / Q000494:pharmacology*; D011720:Pyrazoles / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D013783:Textile Industry; D013784:Textiles; D013844:Thiazoles / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis*
chemical_list: D000081:Acetamides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D004396:Coloring Agents; D006574:Heterocyclic Compounds, 2-Ring; D009570:Nitriles; D011355:Prodrugs; D011720:Pyrazoles; D011743:Pyrimidines; D013844:Thiazoles; D013876:Thiophenes; C547711:enaminonitrile; C031280:pyrazole; D000667:Ampicillin