Synthesis, characterization, and biological activities of 4-imino-3-arylazo-4H-pyrimido[2,1-b][1,3]benzothiazole-2-oles
| Autor: | Erişkin, Selinay, Şener, N., Yavuz, S., Şener, I. |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
drug purification
in vitro study ketoconazole pyrimidine derivative Azo dyes 4 imino 3 (3' chlorophenylazo) 4h pyrimido[2 1 b][1 3]benzothiazole 2 ole Gram negative bacterium Antimicrobial activity minimum inhibitory concentration proton nuclear magnetic resonance antibacterial activity Diazo-coupling reaction ciprofloxacin Gram positive bacterium Pyrimido benzothiazole azo dye controlled study infrared spectroscopy polycyclic aromatic hydrocarbon derivative mass spectrometry structure activity relation 4 imino 3 (4' chlorophenylazo) 4h pyrimido[2 1 b][1 3]benzothiazole 2 ole nonhuman fungus article benzothiazole derivative unclassified drug reaction analysis Solvatochromism drug synthesis imine |
| Popis: | 4-Imino-3,4-dihydro-2H-pyrimido[2,1-b][1,3] benzothiazole-2-one (3) was synthesized by the reaction of 2-aminobenzothiazole with ethyl cyanoacetate in solvent free conditions at 150°C. A series of pyrimido benzothiazole-based azo dyes 4( a-m) were obtained by the coupling of carbocyclic amine-based diazonium chloride with compound (3). The synthesized dyes were purified and characterized by elemental analysis, FT-IR, 1 H NMR, and high-resolution mass spectral data. The solvatochromic behaviors of dyes in various solvents were examined. All the azo dyes exhibited pronounced in vitro antibacterial activities against Gram-positive and Gram-negative bacteria, as well as fungi. The results revealed that most of the compounds exhibited good levels of antibacterial activity. Compounds 4d and 4h showed excellent levels of antimicrobial activity with MIC values of 8.25 μg/mL. © Springer Science+Business Media 2014. |
| Databáze: | OpenAIRE |
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