Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

Nourhène Chouchène (1) , Amani Toumi (1) , Sarra Boudriga (1) , Hayet Edziri (2) , Mansour Sobeh (3) , Mohamed Abdelfattah (4) , Moheddine Askri (1) , Michael Knorr (5) , Carsten Strohmann (6) , Lukas Brieger (6) , Armand Soldera (7)

1 CHPNR - Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité [Monastir]
2 LR99ES27 - Laboratoire des Maladies Transmissibles et Substances Biologiquement Actives [Monastir]
3 UM6P - Université Mohammed VI Polytechnique [Ben Guerir]
4 American University of The Middle East [Eqaila]
5 UTINAM - Univers, Transport, Interfaces, Nanostructures, Atmosphère et environnement, Molécules (UMR 6213)
6 TU - Technische Universität Dortmund [Dortmund]
7 UdeS - Département de chimie [Sherbrooke]

A novel series of 14 spiropyrrolidines bearing thiochroman-4-one/chroman-4-one, and oxindole/acenaphthylene-1,2-dione moieties were synthesized and characterized by spectroscopic techniques, as well as by three X-ray diffraction studies, corroborating the stereochemistry. Quantum chemical calculations studies, using the DFT approach, were performed to rationalize the stereochemical outcome. These N-heterocycles were evaluated for their antibacterial and antifungal activities against some pathogenic organisms. Several compounds displayed moderate to excellent activity towards the screened microbe strains in the study compared to Amoxicillin (AMX), Ampicillin (AMP), and Amphotericin B. Furthermore, a structural activity relationship (SAR) was established considering the synthesized compounds. Pharmacokinetic studies reveal that these derivatives exhibit an acceptable predictive ADMET profile (Absorption, Distribution, Metabolism, Excretion and Toxicity) and good drug-likeness.

Domaines: Chimie

Nourhène Chouchène, Amani Toumi, Sarra Boudriga, Hayet Edziri, Mansour Sobeh, et al.. Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds. Molecules, 2022, 27 (3), pp.582. ⟨10.3390/molecules27030582⟩. ⟨hal-03533865⟩