Synthesis of novel 1,2,3-triazoles prodigiosin fluorescent analogues

Prodigiosin is a secondary metabolite produced by various bacteria including Serratia marcescens1. Studies have demonstrated that this red pigment has antimalarial, immunosuppressive and anticancer properties. Its chemical structure is characterized pyrrolyl dipyrromethene skeleton and this profile belongs to prodigiosenes family, that presents a growing interest in medicinal chemistry because of their biological properties2. The synthetic route was initiated with nitration reaction using pyrrole and nitric acid in acetic anhydride3. Then, reaction was carried out between aldehyde and pyrrole, for synthesis of dipyrromethane4. The nitro group was reduced to amine. The dipyrromethane azide was obtained by diazotization reaction. To synthesis of 1,2,3-triazoles was carried out the copper-catalyzed 1,3-dipolar cycloaddition reaction5. And with complexation with difluoroboryl unit in a base-catalyzed reaction with trifluoroboryl etherate (BF3.OEt2), using triethylamine (TEA) we can synthetize a family of fluorescent compounds.6 The structural elucidation was performed by infrared spectroscopy, 1H and 13C NMR spectroscopy and HRMS.