Abstract
Background: In these study we report here one-pot multi-component and solvent free Mannich reaction of U.V. absorbing material, five member heterocyclic ring system and amides/carbamates has been efficiently catalyzed by recyclable ethyl ammonium nitrate as ionic liquid at ambient temperature to produce mannich compounds in high yields. This method has advantages of mild condition, no environmental pollution, and simple work-up procedures to produce new mannich products 4(a-f). The synthesis of five member based heterocycles has been the point of attraction towards their pronounced biological activities and molecular docking studies.
Methods: The present methodology deals with one pot three component MCR’S reaction of five member based 5-bromothiophene-2-carboxaldehyde, 2-hydroxy-4-methoxybenzophenone and various amides to synthesize new mannich products 4(a-f) in refluxing with ethyl ammonium nitrate as ionic liquid at ambient temperature within 4 to 5 hrs. The docking study was carried out with having receptor in Homo sapiens for antibacterial, Pseudomonas spp. LL2 for anti-fungal and Mycobacterium tuberculosis H37Rv for anti-TB. Results: A series of new synthesized mannich products shows in good to excellent yield (80-86%) via one pot three component reactions. After separation of ionic liquid, obtained products were isolated in good yield by the extraction of products thrice time in ethyl acetate. All of the isolated reaction products were characterised and confirmed through, 1H-NMR, 13C-NMR, Mass spectra and elemental analyses. In obtained products, mainly 4b and 4c compound shows excellent property rather than 4e and 4f and provided desired products in excellent yields may be due to the presence of electron withdrawing groups in five member heterocyclic moiety. Some of the compounds showed in good agreement with its computationally predicted binding energy (MolDock score) with high score in comparison with the rest of the molecules. Conclusion: We have developed a green synthesis, good-yielding and mild reaction protocol for multi component reactions to synthesize new mannich products via one pot three component reaction in solvent free condition at 80ºC. It provided several advantages such as mild conditions and shorter reaction time, simple and eco-friendly operational procedure. A significant activity was observed by the 4c and 4d compounds against four bacterial and fungal strains while compounds 4a, 4e and 4f possess poor activity. The anti-tuberculosis activity of four compounds shows poor activity as compare to the standard drug.Keywords: Multi-component synthesis, heterocyclic compounds, UV absorbing materials, mannich products, molecular docking study.
Graphical Abstract
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