Convenient framework of poly functionalized (E)-2-benzylideno-(Z)-carbazolylideno cyanoacetamides via rearrangements as an efficient antibiofilm inhibitors with SAR study
| Autor: | Karnam Jayarampillai Rajendra Prasad, Jabastin Jayamanoharan, Vladimir N. Nesterov, Perumal Sathiyachandran |
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| Rok vydání: | 2019 |
| Předmět: |
Cyanoacetamide
Stereochemistry Clinical Biochemistry One-pot synthesis Carbazoles Pharmaceutical Science Microbial Sensitivity Tests 01 natural sciences Biochemistry Structure-Activity Relationship chemistry.chemical_compound Aldol reaction Acetamides Gram-Negative Bacteria Drug Discovery Humans Molecular Biology Molecular Structure biology 010405 organic chemistry Aryl Organic Chemistry Biofilm biology.organism_classification In vitro Anti-Bacterial Agents 0104 chemical sciences 010404 medicinal & biomolecular chemistry HEK293 Cells chemistry Biofilms Bacillus megaterium Proton NMR Molecular Medicine Bacteria Bacillus subtilis |
| Zdroj: | Bioorganic & Medicinal Chemistry. 27:777-784 |
| ISSN: | 0968-0896 |
| Popis: | A simple and one-pot approach for the synthesis of highly functionalized novel (E)-2-benzylideno-(Z)-carbazolylideno cyanoacetamide derivatives from different 2-(2′,3′,4′,9′-tetrahydro-carbazol-1′-ylidene)-propanedinitriles and aryl/heteroaryl carbaldehydes via vinylogous aldol reaction. The structures of the molecules were designated by FT-IR, 1H NMR, 13C NMR studies, elemental and X-ray crystallographic analysis. The synthesized pure products have been screened for in vitro antibiofilm inhibitory activity towards antibiotic-resistant pathogenic organisms. All the synthesized compounds showed biofilm inhibition. Promisingly, the moieties 3a, 3d and 3h showed higher antibiofilm activity at biofilm inhibitory concentration (BIC) (200 μg/mL) against bacterial pathogens. Among the three moieties, 3a showed high prospective against E. coli biofilm with minimal and maximal BIC percentage of 32% (10 μg/mL) and 89% (100 μg/mL) and chosen lowest BIC for further evaluation. Also, the 3a generate ROS two fold at 1 h treatment in E. coli biofilm. The 3a exhibited no toxic effect on cell viability upto 75 μg/mL in HEK293 cell lines. The results of the present study reveal that among (E)-2-benzylideno-(Z)-carbazolylideno cyanoacetamides, (E)-2-benzylideno-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-(Z)-α-carbamino-α-cyano-1-ylidene (3a) could be exploited as an excellent antibiofilm agent against carbapenem-resistant E. coli bacteria strains. |
| Databáze: | OpenAIRE |
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