Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds
Nourhène Chouchène,
Amani Toumi,
Sarra Boudriga,
Hayet Edziri,
Mansour Sobeh,
Mohamed A. O. Abdelfattah,
Moheddine Askri,
Michael Knorr,
Carsten Strohmann,
Lukas Brieger,
Armand Soldera
Affiliations
Nourhène Chouchène
Laboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, Tunisia
Amani Toumi
Laboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, Tunisia
Sarra Boudriga
Laboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, Tunisia
Hayet Edziri
Laboratoire des Maladies Transmissibles et des Substances Biologiquement Actives, Faculté de Pharmacie, Monastir 5000, Tunisia
Mansour Sobeh
AgroBioSciences Research, Mohammed VI Polytechnic University, Lot 660–Hay MoulayRachid, Ben Guerir 43150, Morocco
Mohamed A. O. Abdelfattah
College of Engineering and Technology, American University of the Middle East, Kuwait
Moheddine Askri
Laboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, Tunisia
Michael Knorr
Institut UTINAM-UMR CNRS 6213, Université Bourgogne Franche-Comté, 16 Route de Gray, 25030 Besançon, France
Carsten Strohmann
Faculty of Chemistry, Inorganic Chemistry, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany
Lukas Brieger
Faculty of Chemistry, Inorganic Chemistry, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany
Armand Soldera
Laboratory of Physical Chemistry of Matter, Department of Chemistry, Université de Sherbrooke, Sherbrooke, QC J1K 2R1, Canada
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.
