Synthesis and Antifungal Activity of 4‐ and 6‐(1 H ‐Pyrrol‐1‐yl) Coumarins, and their Thiocyanato Derivatives

BRITES, NATHAN P.; DILELIO, MARINA C.; MARTINS, GUILHERME M.; CARMO, GABRIELE DO; MOREL, ADEMIR F.; KAUFMAN, TEODORO S.; SILVEIRA, CLAUDIO C.

ChemistrySelect

Wiley

Lugar: Nueva York; Año: 2019 vol. 4 p. 5398 - 5406

2365-6549

Facile and efficient syntheses of 4-(1H-pyrrol-1-yl)-coumarinsand 6-(1H-pyrrol-1-yl)-coumarins from the corresponding aminocoumarinsare reported. The transformations were optimizedand their corresponding scope and limitations were assessed.Selected (1H-pyrrol-1-yl)-coumarins were further subjected to amild thiocyanation, undergoing selective functionalization onthe pyrrole nucleus. A set of 10 differently substitutedcompounds was submitted to activity testing against variousfungal strains. It was found that the introduction of a SCNmoiety increased the antifungal activity, turning some compoundsinto fungicidal agents, to the point that one of thethiocyanato derivatives displayed an antifungal profile comparableto those of fluconazole and nystatin.