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

Abstract

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), 1H nuclear magnetic resonance, 13C 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.