N‐Sulfonyl‐1,2,3,4‐tetrahydroisoquinoline Derivatives: Synthesis, Antimicrobial Evaluations, and Theoretical Insights

RINALDI TOSI, MARTÍN; PALERMO, VALERIA; GIANNINI, FERNANDO; FERNÁNDEZ-BALDO, MARTÍN; DIAZ, JORGE; LIMA, BEATRIZ; FERESIN, GABRIELA; ROMANELLI, GUASTAVO; BALDONI, HÉCTOR ARMANDO

Chemistry and Biodiversity

WILEY-V C H VERLAG GMBH

Año: 2023

1612-1872

Microbial contamination remains a significant economic challenge in the food 2 industry, emphasizing the need for innovative antimicrobial solutions. In this study, we 3 synthesized N-sulphonyl-1,2,3,4-tetrahydroisoquinolines (NSTHIQ) derivatives using an 4 environmentally friendly Preyssler heteropolyacid catalyst, obtaining moderate to high 5 yields (35-91%) under mild conditions. Two derivatives (5 and 6) exhibited significant 6 antifungal properties against various fungal species, including Aspergillus spp, Penicillium 7 spp, and Botrytis cinerea. ADMET (Absorption, Distribution, Metabolism, Excretion, and 8 Toxicity) analysis revealed the absence of hepatic toxicity in all compounds, making 9 derivatives 2, 3, 4, and 5potential candidates for further development. However, 10 derivatives 6 and 7 exhibited immunotoxicity. In support of our experimental findings, 11 reactivity indices were computed using Density Functional Theory principles, deriving 12 valuable insights into the chemical properties of these derivatives. This study underscores 13 the potential of NSTHIQ compounds as potent antifungal agents, coupled with the 14 importance of employing environmentally friendly catalysts in drug discovery