We describe the synthesis of the novel 2-(1,5-dimethyl-4-oxo-hexyl)-3-hydroxy-5-methyl-6-pyrrolyl-1,4-benzoquinone 2 from the natural product perezone 1. The anion–guest properties of the new compound were evaluated in the presence of fluoride, chloride, bromide and iodide tetrabutylammonium salts using 1H NMR titration techniques in deuterated dichloromethane or dimethylformamide. The title compound showed interesting colorimetric behavior in the presence of inorganic salts.
Molecular modeling applies several computational chemistry tools as molecular docking; this latter has been useful in medicinal chemistry for prediction of interactions between small ligands and biological targets measuring angles, enthalpy and other physicalchemical properties involved in the supramolecular entities. In this chapter, we present molecular docking advances with a perspective to the improvement of parameterization including halogen bonding interactions (XB) and the modification of scoring functions based on halogen sigma-hole polarization. At the same time, we have included the current computational methods to study halogen bonding that increased the accuracy of predicted entities. Finally, we present examples of the main force fields including electronic distribution and modifications for halogen atoms.
Perezone is a naturally occurring hydroxyquinone that has been deeply studied from different chemical aspects, such as therapeutics, electrochemistry, physical–chemical properties, or synthetic approaches that turn it an attractive template for new semisynthetic derivatives with a wide range of purposes. Herein, we describe a facile synthetic pathway to obtain new perezone derivatives by the addition of a pyrrole moiety that can be used for ion recognition. Compounds 2–4 showed the capability to interact with several anions and M 2+ cations as separate events that result in colorimetric changes. Moreover, the compounds can behave as heteroditopic receptors. Besides, a previous interaction between fluoride ions and perezone derivatives triggered a successful recognition of M 2+ ions, remarking Ni 2+ as the most interesting phenomenon. These results project the compounds as potential colorimetric receptors for nickel ions in complex solutions.
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