N-Sulfonyl-1,2,3,4-tetrahydroisoquinoline Derivatives: Synthesis, Antimicrobial Evaluations, and Theoretical Insights.
ADMET
antibacterial
antifungal
sulfonamide
tetrahydroisoquinolines
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Nov 2023
Nov 2023
Historique:
received:
21
06
2023
accepted:
05
10
2023
medline:
29
11
2023
pubmed:
6
10
2023
entrez:
5
10
2023
Statut:
ppublish
Résumé
Microbial contamination remains a significant economic challenge in the food industry, emphasizing the need for innovative antimicrobial solutions. In this study, we synthesized N-sulfonyl-1,2,3,4-tetrahydroisoquinolines (NSTHIQ) derivatives using an environmentally friendly Preyssler heteropolyacid catalyst, obtaining moderate to high yields (35-91 %) under mild conditions. Two derivatives (5 and 6) exhibited significant antifungal properties against various fungal species, including Aspergillus spp, Penicillium spp, and Botrytis cinerea. ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) analysis revealed the absence of hepatic toxicity in all compounds, making derivatives 2, 3, 4, and 5 potential candidates for further development. However, derivatives 6 and 7 exhibited immunotoxicity. In support of our experimental findings, reactivity indices were computed using Density Functional Theory principles, deriving valuable insights into the chemical properties of these derivatives. This study underscores the potential of NSTHIQ compounds as potent antifungal agents, coupled with the importance of employing environmentally friendly catalysts in drug discovery.
Identifiants
pubmed: 37798253
doi: 10.1002/cbdv.202300905
doi:
Substances chimiques
Anti-Infective Agents
0
Antifungal Agents
0
Tetrahydroisoquinolines
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300905Subventions
Organisme : National Scientific and Technical Research Council - Argentina
ID : PIP0111
Organisme : National Scientific and Technical Research Council - Argentina
ID : PIP090CO
Organisme : CCAD-UNC
Organisme : SNCAD-MinCyT
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
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