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

M. TOSI; V. PALERMO; F. GIANNINI; M. BALDO; J. DIAZ; B. LIMA; G. FERESIN; G. ROMANELLI; H. BALDONI

Chemistry and Biodiversity

John Wiley and Sons Inc

Año: 2023 vol. 20

Microbial contamination remains a significant economic chal-lenge in the food industry, emphasizing the need for innovativeantimicrobial solutions. In this study, we synthesized N-sulfonyl-1,2,3,4-tetrahydroisoquinolines (NSTHIQ) derivatives using anenvironmentally friendly Preyssler heteropolyacid catalyst, ob-taining moderate to high yields (35–91%) under mild con-ditions. Two derivatives (5 and 6) exhibited significant anti-fungal properties against various fungal species, includingAspergillus spp, Penicillium spp, and Botrytis cinerea. ADMET(Absorption, Distribution, Metabolism, Excretion, and Toxicity)analysis revealed the absence of hepatic toxicityin allcompounds, making derivatives 2, 3, 4, and 5 potentialcandidates for further development. However, derivatives 6 and7 exhibited immunotoxicity. In support of our experimentalfindings, reactivity indices were computed using Density Func-tional Theory principles, deriving valuable insights into thechemical properties of these derivatives. This study underscoresthe potential of NSTHIQ compounds as potent antifungalagents, coupled with the importance of employing environ-mentally friendly catalysts in drug discovery.