Organocatálise na síntese de 1,2,3-triazóis derivados de sulfonamidas

Abstract

In this work we described a methodology for the preparation of N-(4 sulfamoylphenyl)-1H-1,2,3-triazole-4-carboxamides 3 through the use of 1,8 diazabicyclo[5.4.0]undec-7-ene (DBU) as organocatalyst from N-(4 sulfamoyl)butanamides 1 and aryl azides 2 (Scheme 1). After determining the best organocatalyst to obtain the desired products, the method was applied to different substrates 1 and a range of aryl azides 2 with electron donor and withdrawn groups. The protocol proved to be efficient for obtaining new molecules containing the triazole nucleus and sulfonamide group in their structure, presenting a large tolerance to different functional groups. Furthermore, all the products were analyzed trough molecular docking in their binding affinity to Myeloperoxidase (MPO), which six of them performed interactions with the catalytic core of this enzyme. In addition, the selected compounds had higher docking score values than Meloxicam, a worldwide consumed anti-inflammatory drug. Thus, the molecules developed showed a great potential to use in the inhibition of MPO, which makes them very relevant therapeutic targets.