Design of new hybrids of fullerenes decorated with molecular fragments of chemical and biological relevance
Keywords:
fullerenes, cyclopropanation, hybrid systems, steroids, carbohydratesAbstract
Introduction: In recent years, fullerenes have acquired great interest since their structure enables the development of novel chemistry based on the unique characteristics of these molecules. Because it is reported the existence of fullerenic conjugates with steroids or sugars that show interesting chemical, physical, and biological properties, it is of interest to generate synthetic strategies to develop new compounds.
Objectives: To synthesize hybrids of the methanofullerene type functionalized with steroidal fragments and derivatives of monosaccharides of chemical and biological interest, using the cyclopropanation reaction, and to predict their potential use in medical chemistry and materials science, through the study of their properties by theoretical and experimental methods.
Methods: They are fundamentally based on the synthesis of hybrid methanofullerenes functionalized with steroids, monosaccharides, and seleno-sugars, using the Bingel-Hirsch cyclopropanation reaction.
Results: The covalent union of the conjugates to [60]fullerene allowed obtaining 12 new hybrid compounds. The described procedure was extended to H2@C60 and [70]fullerene to obtain the first steroidal chimeras of these fullerenes. All compounds were characterized using spectroscopic techniques and mass spectrometry, which allowed confirming its structures. They were also studied the influence of the different substituents of the hybrids on their thermal properties, electrochemical behavior, and aggregation in water. Using theoretical methods, it was studied, based on their supramolecular interactions, the potential use of one of the synthesized hybrids as an electron acceptor for organic solar cells. Molecular docking was used to determine the potential application of these derivatives as viral protease inhibitors.
Conclusions: Molecular hybridization from steroids, carbohydrates, and fullerenes makes it possible to obtain molecules with potential applications in both medical chemistry and materials science.Downloads
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