Abstract
3-Phenylcoumarins are a family of heterocyclic molecules that are widely used in both organic and medicinal chemistry. In this overview, research on this scaffold, since 2010, is included and discussed, focusing on aspects related to its natural origin, synthetic procedures and pharmacological applications. This review paper is based on the most relevant literature related to the role of 3-phenylcoumarins in the design of new drug candidates. The references presented in this review have been collected from multiple electronic databases, including SciFinder, Pubmed and Mendeley.
Highlights
Academic Editors: Jean-Marc Sabatier, Diego Muñoz-Torrero, Simona Rapposelli, Michael Gütschow, Maria Emília de Sousa and Luciano Saso
For the synthesis of 3-phenylcoumarins, three main methodologies have been used in the past decade: coumarin coupling with the benzene ring, construction of the coumarin bicyclic system and construction of the benzene ring at position 3
The carbonylation has been carried out for the synthesis of 3-aryl-4-(arylethynyl)coumarins from 2-iodoaryl 2-arylacetates and arylacetylenes via a Sonogashira coupling–intramolecular aldol cascade reaction, in the presence of bis(triphenylphosphine)palladium chloride [Pd(PPh3)2(Cl)2] as the catalyst [52]. 3-Arylcoumarins have been obtained from the condensation of electron-rich arenes with allenes, in the presence of trifluoromethanesulfonic acid (TfOH), in good yield
Summary
3-Phenylcoumarins have been used by several research groups in the search for new chemical entities with potential in the discovery of new therapeutic solutions for several diseases. Different molecular spots that may be modified, with different reactivities, allow for a huge number of different derivatives with different properties This scaffold can be considered an isostere of the isoflavone in which the carbonyl group is translated from position 4 to position 2 on the pyran ring (Figure 1). Isoflavones are produced almost exclusively by the members of the bean family Fabaceae (Leguminosae) It can be considered a coumarin-resveratrol hybrid. A connection of 3-phenylcoumarins can be established ( it is more from a structural or steric point of view) with steroid hormones, especially with estrogens, due to the aromatization of the A ring For these reasons, 3-phenylcoumarins (Figure 1) are considered a privileged scaffold in medicinal chemistry. Very brief references to their physicochemical properties or their application as fluorescence probes, a field in which references are quite abundant, have been included
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