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

Molecules

Mansour Sobeh¹  Mohamed A. O. Abdelfattah²  Lukas Brieger³  Carsten Strohmann³  Michael Knorr⁴  Hayet Edziri⁵  Nourhène Chouchène⁶  Amani Toumi⁶  Sarra Boudriga⁶  Moheddine Askri⁶  Armand Soldera⁷ 

[1] AgroBioSciences Research, Mohammed VI Polytechnic University, Lot 660–Hay MoulayRachid, Ben Guerir 43150, Morocco;College of Engineering and Technology, American University of the Middle East, Kuwait;Faculty of Chemistry, Inorganic Chemistry, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany;Institut UTINAM-UMR CNRS 6213, Université Bourgogne Franche-Comté, 16 Route de Gray, 25030 Besançon, France;Laboratoire des Maladies Transmissibles et des Substances Biologiquement Actives, Faculté de Pharmacie, Monastir 5000, Tunisia;Laboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, Tunisia;Laboratory of Physical Chemistry of Matter, Department of Chemistry, Université de Sherbrooke, Sherbrooke, QC J1K 2R1, Canada;

关键词: [3+2] cycloaddition;    thiochroman-4-one;    chroman-4-one;    spiropyrrolidine;    crystal structure;    DFT;   

DOI  :  10.3390/molecules27030582

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown