Coumarin and its derivatives are widely used as scaffolds in the synthesis of new heterocyclic systems. This review focuses on current developments in the synthesis of heterocyclic coumarin compounds. Numerous approaches especially involving nanoparticle catalysts have been developed to get new bioactive coumarin derivatives endowed with pharmacological and biological activities. The present work describes the reactivity and the new strategies using various catalysts for the synthesis of coumarin and its derivatives reported in the literature and their biological properties.
The versatility of N‐methyl‐nitroindazolylacetonitriles as templates for further modifications was evidenced by their successfully alkylation with a series of alkyl halides using DBU as base affording the monoalkylated derivatives in high yields. Another synthetic strategy used to modify the nitroindazolylacetonitrile derivatives was the Knoevenagel condensation with a series of aldehydes in the presence of piperidine; such condensation allowed the preparation of the desired products in good to excellent yields. The reaction of a series of nitroindazolylacetonitriles with salicylaldehyde showed to be an efficient and fast methodology to prepare chromenone‐imine‐indazoles (83‐92%), which by acid hydrolysis were converted into the corresponding chromenone‐indazole derivatives (88‐94%). The structures of derivatives 8 h, 8 l and 10 were unequivocally confirmed by single crystal X‐ray diffraction. The drug‐likeness properties of the compounds were evaluated in silico and none of the tested nitroindazolylacetonitriles violated the Lipinski's “rule of five”. The antiproliferative activity against human cervical cancer cells (HeLa) and normal human dermal fibroblasts was evaluated by MTT assay and revealed that compounds 7 b, 8 d and 14 a are those who presented higher antiproliferative effect against HeLa cancer cells.
Efficient synthesis of new N-methylnitroindazolylacetonitriles and their ability to switch between tautomeric forms in the presence of anionic species.
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