Synthesis, spectral characterization, and effective antifungal evaluation of 1H-tetrazole containing 1,3,5-triazine dendrimers

Thirteen, 1,3,5-triazine core containing tetrazole dendrimeric chalcones have been synthesized in three steps. In the first step (1-(4-(1H-tetrazole-1-yl)phenyl)ethanone) is synthesized from sodium azide and triethyl orthoformate. In the second step, the first-generation of dendrimer, 2,4,6-(tris(te...

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Veröffentlicht in:Medicinal chemistry research 2016-09, Vol.25 (9), p.1916-1924
Hauptverfasser: Vembu, Sandhirakasu, Pazhamalai, Srinivasan, Gopalakrishnan, Mannathusamy
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Sprache:eng
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Zusammenfassung:Thirteen, 1,3,5-triazine core containing tetrazole dendrimeric chalcones have been synthesized in three steps. In the first step (1-(4-(1H-tetrazole-1-yl)phenyl)ethanone) is synthesized from sodium azide and triethyl orthoformate. In the second step, the first-generation of dendrimer, 2,4,6-(tris(tetrazole-1-yl-(4-acetylphenyl))-1,3,5-triazine( G1 ) is generated from cyanuric chloride and 4-tetrazoylacetophenone by Friedel–Crafts reaction. In the third step, 2,4,6-tris(tetrazol-1-yl-(4-phenyl(3-arylpropene-1-on-1-yl))-1,3,5-triazine( G2 ) dendrimers are prepared from G1 by Claisen–Schmidt reaction with appropriate aldehydes in ethanol at room temperature. The synthesized compounds ( G2 , 7a–m) are characterized by Fourier transform infrared (FT-IR), Mass, Matrix-assisted laser ionization Time-of-flight (MALDI-TOF), 1 H nuclear magnetic resonance, 13 C nuclear magnetic resonance, and elemental analysis. Antifungal activities of triazine-based dendrimeric chalcones ( 7a–m ) are investigated by minimum inhibition concentration method at different concentrations. Some compounds exhibit moderate activities against tested organisms. Compounds 7b , 7c , and 7f showed good activities and 7l and 7m are emerged as lead molecules showing excellent antifungal activities against a panel of fungi.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-016-1627-6