Development of novel adenosine receptor ligands based on the 3-amidocoumarin scaffold

Evaluation of Trypanocidal and Antioxidant Activities of a Selected Series of 3-amidocoumarins

“…The described derivatives were efficiently synthesized according to the protocol outlined in Scheme 1. Coumarins 1-9 were prepared starting from 3-aminocoumarin or from 4-hydroxy-3-aminocoumarin, which were synthesized as previously described [17][18][19][20][21][22].…”

“…Reagents and conditions: a) hydrogen gas (H2), Ethanol as solvent, Palladium on carbon (Pd/C) used as a catalyst, stirring at room temperature for 5 h; b) Substituted acid chloride (R2COCl), pyridine, dichloromethane, 0 °C to room temperature, overnight. All the details are described in references [17][18][19][20][21][22].…”

“…Starting materials and reagents were obtained from commercial suppliers and were used without further purifica-tion (Sigma-Aldrich). The described derivatives were efficiently synthesized according to the protocols outlined in Scheme 1 [17][18][19][20][21][22].…”

Adenosine Receptor Ligands: Coumarin–Chalcone Hybrids as Modulating Agents on the Activity of hARs

“…Having in mind that both the coumarin and chalcone nuclei are structurally close to flavonoids, the design of novel AR ligands based on their scaffolds emerged as an interesting idea. Our study was also motivated by the structural similarity between the coumarin and the chromone scaffolds, which were previously described as AR ligands [ 35 , 36 ], and by the similarities with some coumarin derivatives previously described in our group [ 37 , 38 , 39 , 40 , 41 , 42 ]. In this context, we focused our attention on the 3-benzoylcoumarin core, considered as a hybrid scaffold in which the chalcone is fixed in a trans conformation through the double bond of the pyrone ring of the coumarin skeleton ( Figure 1 ), presenting a more restricted conformation compared to the previously described coumarin–chalcone hybrids [ 36 ].…”

Coumarins and adenosine receptors: New perceptions in structure–affinity relationships

“…In this context, a number of coumarin-based derivatives, in particular 3-arylcoumarins, have been reported by our group as inspiring ligands (Figure 1). [12][13][14][15] Preliminary structure-activity relationship studies indicated that the nature of the substituents located in the coumarin ring, the presence or absence of a spacer between the pyrone ring and an aryl or alkyl side chain can modulate their affinity and selectivity, in particular towards A 3 AR. To gain insight over the structural requirements needed for the development of a potent and selective AR coumarin-based ligand, a series of 6-substituted coumarin derivatives was synthesized, characterized and pharmacologically evaluated.…”