Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds
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 calculatio...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/3/582 |
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| author | Nourhène Chouchène Amani Toumi Sarra Boudriga Hayet Edziri Mansour Sobeh Mohamed A. O. Abdelfattah Moheddine Askri Michael Knorr Carsten Strohmann Lukas Brieger Armand Soldera |
| author_facet | Nourhène Chouchène Amani Toumi Sarra Boudriga Hayet Edziri Mansour Sobeh Mohamed A. O. Abdelfattah Moheddine Askri Michael Knorr Carsten Strohmann Lukas Brieger Armand Soldera |
| author_sort | Nourhène Chouchène |
| collection | DOAJ |
| description | 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 <i>N</i>-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. |
| first_indexed | 2024-03-09T23:31:23Z |
| format | Article |
| id | doaj.art-a6ef0b31584148beaefe38ae6e06bde9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:31:23Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a6ef0b31584148beaefe38ae6e06bde92023-11-23T17:09:06ZengMDPI AGMolecules1420-30492022-01-0127358210.3390/molecules27030582Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one ScaffoldsNourhène Chouchène0Amani Toumi1Sarra Boudriga2Hayet Edziri3Mansour Sobeh4Mohamed A. O. Abdelfattah5Moheddine Askri6Michael Knorr7Carsten Strohmann8Lukas Brieger9Armand Soldera10Laboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, TunisiaLaboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, TunisiaLaboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, TunisiaLaboratoire des Maladies Transmissibles et des Substances Biologiquement Actives, Faculté de Pharmacie, Monastir 5000, TunisiaAgroBioSciences Research, Mohammed VI Polytechnic University, Lot 660–Hay MoulayRachid, Ben Guerir 43150, MoroccoCollege of Engineering and Technology, American University of the Middle East, KuwaitLaboratory of Heterocyclic Chemistry Natural Product and Reactivity (LR11ES39), Department of Chemistry, Faculty of Science of Monastir, University of Monastir, Monastir 5019, TunisiaInstitut UTINAM-UMR CNRS 6213, Université Bourgogne Franche-Comté, 16 Route de Gray, 25030 Besançon, FranceFaculty of Chemistry, Inorganic Chemistry, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, GermanyFaculty of Chemistry, Inorganic Chemistry, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, GermanyLaboratory of Physical Chemistry of Matter, Department of Chemistry, Université de Sherbrooke, Sherbrooke, QC J1K 2R1, CanadaA 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 <i>N</i>-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.https://www.mdpi.com/1420-3049/27/3/582[3+2] cycloadditionthiochroman-4-onechroman-4-onespiropyrrolidinecrystal structureDFT |
| spellingShingle | Nourhène Chouchène Amani Toumi Sarra Boudriga Hayet Edziri Mansour Sobeh Mohamed A. O. Abdelfattah Moheddine Askri Michael Knorr Carsten Strohmann Lukas Brieger Armand Soldera Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds Molecules [3+2] cycloaddition thiochroman-4-one chroman-4-one spiropyrrolidine crystal structure DFT |
| title | Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds |
| title_full | Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds |
| title_fullStr | Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds |
| title_full_unstemmed | Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds |
| title_short | Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds |
| title_sort | antimicrobial activity and dft studies of a novel set of spiropyrrolidines tethered with thiochroman 4 one chroman 4 one scaffolds |
| topic | [3+2] cycloaddition thiochroman-4-one chroman-4-one spiropyrrolidine crystal structure DFT |
| url | https://www.mdpi.com/1420-3049/27/3/582 |
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